[ CAS No. 42823-46-1 ] {[proInfo.proName]}

Name: 42823-46-1|4-Guanidinobenzoic acid hydrochloride|97%
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SKU: A211798
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Quality Control of [ 42823-46-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 42823-46-1 ]

SDS Specification

Alternatived Products of [ 42823-46-1 ]

Product Details of [ 42823-46-1 ]

CAS No. :	42823-46-1	MDL No. :	MFCD00040587
Formula :	C₈H₁₀ClN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YETFLAUJROGBMC-UHFFFAOYSA-N
M.W :	215.64	Pubchem ID :	3084875
Synonyms :

Calculated chemistry of [ 42823-46-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	53.88
TPSA :	101.7 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.4
Log Po/w (WLOGP) :	-2.59
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	-0.15
Consensus Log Po/w :	-0.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	1.23 mg/ml ; 0.0057 mol/l
Class :	Soluble
Log S (Ali) :	-3.14
Solubility :	0.156 mg/ml ; 0.000725 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.15
Solubility :	15.4 mg/ml ; 0.0716 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 42823-46-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 42823-46-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 42823-46-1 ]
Downstream synthetic route of [ 42823-46-1 ]

[ 42823-46-1 ] Synthesis Path-Upstream 1~5

1
[ 420-04-2 ]
[ 150-13-0 ]
[ 42823-46-1 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: With hydrogenchloride In water at 20 - 100℃; Stage #2: With potassium carbonate In water for 0.5 h;	To a stirred suspension of 4-aminobenzoic acid (50 g, 0.364 mole) in a mixture of concentrated HCl/water (46 mL/283 mL) was added cyanamide (35 g, 0.839 mole) at room temperature. The reaction mixture was heated at 100° C. for 6 hours. The reaction mixture was then allowed stand at room temperature (without stirring) for 16 hours. The precipitated solid was filtered and washed with water (100 mL). The solid was taken in aqueous K₂CO₃solution (30 g in 400 mL of water) and stirred for 30 minutes. The solid was filtered, washed with water (2.x.50 mL) and dried under vacuum to provide Int-2A (35 g, 53percent) as white solid. ¹H NMR (200 MHz, dmso-d₆): δ 8.40-8.21 (bs, 2H), 7.93 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H). Mass (m/z): 180.1 [M⁺+1]. To a stirred suspension of Int-2A (35 g, 195.5 mmol) in methanol (350 mL) was added acetyl chloride (35 mL, 490 mmol) dropwise at 0° C. under inert atmosphere over a period of 20 minutes. The reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material (by thin layer chromatography (TLC)), the reaction mixture was neutralized using solid NaHCO₃at 0° C. Solid (excess NaHCO₃) was filtered and filtrate was evaporated under vacuum to get crude compound. The crude compound was washed with EtOAc (100 mL) to afford pure Int-2B (35 g, 92percent) as white solid. ¹H NMR (200 MHz, dmso-d₆): δ 8.45-8.23 (bs, 2H), 7.98 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.8 Hz, 2H), 3.83 (s, 3H). Mass (m/z): 194.1 [M⁺+1].

Reference： [1] Patent: US2010/29638, 2010, A1, . Location in patent: Page/Page column 62
[2] European Journal of Medicinal Chemistry, 1996, vol. 31, # 11, p. 895 - 899

2
[ 156-62-7 ]
[ 150-13-0 ]
[ 42823-46-1 ]

Yield	Reaction Conditions	Operation in experiment
45.8%	With hydrogenchloride In water at 80℃; for 3 h; Cooling with ice	1) 100 mL of concentrated hydrochloric acid was added to 250 mL of a three-necked reaction flask and mechanically stirred.2) 10 g of p-aminobenzoic acid and 30 g of lime nitrogen were mixed uniformly.3) The mixture was slowly added to the reaction flask under ice-water bath and stirred into a mixture (insoluble).4) The reaction mixture was allowed to warm to 80 ° C for 3 hours.5) 20 g of lime nitrogen was slowly added to the reaction flask and incubated for 3 hours.6) Check whether the pH of the reaction solution is neutral.7) The reaction solution in the reaction flask was concentrated under reduced pressure at 80 ° C to dryness to give a dark brown solid.8) The solid was subjected to Soxhlet extraction for 3 to 4 hours using 200 mL of methyl tert-butyl ether.9) The methyl tert-butyl ether solution was added to dry anhydrous sodium sulfate.10) A solution of dried methyl tert-butyl ether was passed through the dry HCl gas at room temperature to precipitate a solid.11) The above-mentioned precipitated solid was carefully filtered and the precipitated solid was washed with an appropriate amount of methyl t-butyl ether to obtain a wet product.12) The wet product was poured into a vacuum oven at 45 ° C to give a solution of guanidinobenzoate (7.2 g, 45.8percent).

Reference： [1] Patent: CN106543041, 2017, A, . Location in patent: Paragraph 0023-0037

3
[ 1627898-15-0 ]
[ 42823-46-1 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3565 - 3569

4
[ 150-13-0 ]
[ 42823-46-1 ]

Reference： [1] Patent: US5086069, 1992, A,

5
[ 623-00-7 ]
[ 42823-46-1 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3565 - 3569

[ 42823-46-1 ] Synthesis Path-Downstream 1~88

1
[ 120-47-8 ]
[ 42823-46-1 ]
[ 89022-08-2 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

2
[ 148-24-3 ]
[ 42823-46-1 ]
[ 89022-10-6 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

3
[ 150-19-6 ]
[ 42823-46-1 ]
[ 79126-26-4 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

4
[ 106-44-5 ]
[ 42823-46-1 ]
[ 57438-34-3 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

5
[ 99-89-8 ]
[ 42823-46-1 ]
[ 99966-54-8 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

6
[ 97-53-0 ]
[ 42823-46-1 ]
[ 89022-12-8 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

7
[ 402-45-9 ]
[ 42823-46-1 ]
[ 99966-60-6 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

8
[ 98-54-4 ]
[ 42823-46-1 ]
[ 99966-55-9 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

9
[ 873-62-1 ]
[ 42823-46-1 ]
[ 100019-78-1 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

10
[ 98-17-9 ]
[ 42823-46-1 ]
[ 99966-52-6 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

11
[ 136-77-6 ]
[ 42823-46-1 ]
[ 89035-73-4 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

12
[ 103-90-2 ]
[ 42823-46-1 ]
[ 79119-49-6 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

13
[ 19438-10-9 ]
[ 42823-46-1 ]
[ 99966-53-7 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

14
[ 42823-46-1 ]
[ 82957-06-0 ]
4-Guanidino-benzoic acid 6-carbamimidoyl-naphthalen-2-yl ester; compound with carbonic acid [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 1458 - 1471

15
[ 42823-46-1 ]
[ 84429-24-3 ]
[ 80532-07-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4466 - 4477

16
[ 42823-46-1 ]
[ 84437-28-5 ]
[ 80532-08-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4466 - 4477

17
[ 42823-46-1 ]
[ 767-00-0 ]
[ 104-15-4 ]
[ 99966-61-7 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

18
[ 42823-46-1 ]
[ 122-94-1 ]
[ 99966-59-3 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

19
[ 106-41-2 ]
[ 42823-46-1 ]
[ 104-15-4 ]
[ 100019-80-5 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

20
[ 89-83-8 ]
[ 42823-46-1 ]
[ 104-15-4 ]
[ 89022-14-0 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

21
[ 42823-46-1 ]
[ 104-15-4 ]
[ 106-48-9 ]
[ 99966-57-1 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

22
[ 42823-46-1 ]
[ 150-76-5 ]
[ 99966-58-2 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

23
[ 42823-46-1 ]
[ 90-05-1 ]
[ 99966-51-5 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

24
[ 42823-46-1 ]
[ 99-76-3 ]
[ 26173-48-8 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

25
[ 42823-46-1 ]
[ 65-45-2 ]
[ 89022-09-3 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

26
[ 42823-46-1 ]
[ 2321-07-5 ]
[ 83616-10-8 ]
[ 83616-11-9 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 7299 - 7306

27
[ 42823-46-1 ]
[ 108-95-2 ]
[ 35695-21-7 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

28
[ 42823-46-1 ]
[ 119-36-8 ]
[ 89022-11-7 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

29
[ 42823-46-1 ]
[ 16060-65-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

30
[ 420-04-2 ]
[ 150-13-0 ]
[ 42823-46-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; In ethanol; at 50 - 78℃;	Add 20 g of para-aminobenzoic acid to 100 ml of ethanol,Slowly add 20ml of 30% hydrochloric acid ethanol and warm to 50 C.Cyanamide was added dropwise 30% 40g, dropwise, the reaction 75 ± 3 5-7 hours.After the reaction was completed, the solution was concentrated to dryness under reduced pressure at 50 C, 50 ml of ethanol and 10 ml of 30% hydrochloric acid ethanol were added, filtered with stirring, and dried.Recrystallize with 5-10 times the volume of 20% ethanol solution to obtain pure product.The yield of the obtained 4-guanidinobenzoic acid hydrochloride was 85%.
53%		To a stirred suspension of 4-aminobenzoic acid (50 g, 0.364 mole) in a mixture of concentrated HCl/water (46 mL/283 mL) was added cyanamide (35 g, 0.839 mole) at room temperature. The reaction mixture was heated at 100 C. for 6 hours. The reaction mixture was then allowed stand at room temperature (without stirring) for 16 hours. The precipitated solid was filtered and washed with water (100 mL). The solid was taken in aqueous K2CO3 solution (30 g in 400 mL of water) and stirred for 30 minutes. The solid was filtered, washed with water (2×50 mL) and dried under vacuum to provide Int-2A (35 g, 53%) as white solid. 1H NMR (200 MHz, dmso-d6): delta 8.40-8.21 (bs, 2H), 7.93 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H). Mass (m/z): 180.1 [M++1]. To a stirred suspension of Int-2A (35 g, 195.5 mmol) in methanol (350 mL) was added acetyl chloride (35 mL, 490 mmol) dropwise at 0 C. under inert atmosphere over a period of 20 minutes. The reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material (by thin layer chromatography (TLC)), the reaction mixture was neutralized using solid NaHCO3 at 0 C. Solid (excess NaHCO3) was filtered and filtrate was evaporated under vacuum to get crude compound. The crude compound was washed with EtOAc (100 mL) to afford pure Int-2B (35 g, 92%) as white solid. 1H NMR (200 MHz, dmso-d6): delta 8.45-8.23 (bs, 2H), 7.98 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.8 Hz, 2H), 3.83 (s, 3H). Mass (m/z): 194.1 [M++1].

Reference： [1]Patent: CN110330447,2019,A .Location in patent: Paragraph 0047-0051
[2]Patent: US2010/29638,2010,A1 .Location in patent: Page/Page column 62
[3]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

31
[ 21715-90-2 ]
[ 42823-46-1 ]
4-guanidinobenzoic acid 3,5-dioxo-4-azatricyclo[5.2.1.0.2,6)deca-8-en-4-yl ester hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

32
[ 42823-46-1 ]
{(S)-4-(2-Amino-acetyl)-3-[(4-guanidino-benzoylamino)-methyl]-2-oxo-piperazin-1-yl}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

33
[ 42823-46-1 ]
{(S)-4-(2-Amino-acetyl)-3-[2-(4-guanidino-benzoylamino)-ethyl]-2-oxo-piperazin-1-yl}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

34
[ 42823-46-1 ]
{(S)-4-(2-Amino-acetyl)-3-[3-(4-guanidino-benzoylamino)-propyl]-2-oxo-piperazin-1-yl}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

35
[ 42823-46-1 ]
[ 1026864-00-5 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

36
[ 42823-46-1 ]
{(S)-4-(2-Benzyloxycarbonylamino-acetyl)-3-[2-(4-guanidino-benzoylamino)-ethyl]-2-oxo-piperazin-1-yl}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

37
[ 42823-46-1 ]
[ 356535-18-7 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

38
[ 42823-46-1 ]
{(S)-4-[2-(4-Carbamimidoyl-benzoylamino)-acetyl]-3-[(4-guanidino-benzoylamino)-methyl]-2-oxo-piperazin-1-yl}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

39
[ 42823-46-1 ]
(S)-4-(4-amidinobenzoylamino)acetyl-3-[2-(4-guanidinobenzoylamino)]ethyl-2-oxopiperazine-1-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

40
[ 42823-46-1 ]
{(S)-4-[2-(4-Carbamimidoyl-benzoylamino)-acetyl]-3-[3-(4-guanidino-benzoylamino)-propyl]-2-oxo-piperazin-1-yl}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2438 - 2450

41
[ 42823-46-1 ]
Guanidinobenzoic acid mesylate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

42
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(morpholine-4-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

43
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(4-methyl-piperazine-1-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

44
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(4-isopropyl-piperazine-1-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

45
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(4-propyl-piperazine-1-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

46
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(4-sec-butyl-piperazine-1-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

47
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-[4-(1-methyl-butyl)-piperazine-1-carbonyl]-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

48
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(4-hexyl-piperazine-1-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

49
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(4-benzyl-piperazine-1-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

50
[ 42823-46-1 ]
C₂₄H₂₉N₅O₅*CH₄O₃S [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

51
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-[4-(2-diethylamino-ethyl)-piperazine-1-carbonyl]-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

52
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-[4-(2-ethoxycarbonyl-ethyl)-piperazine-1-carbonyl]-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

53
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-(4-diethylcarbamoylmethyl-piperazine-1-carbonyl)-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

54
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-[4-(3-ethoxycarbonyl-propyl)-piperazine-1-carbonyl]-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

55
[ 42823-46-1 ]
C₂₈H₂₉N₅O₅*CH₄O₃S [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

56
[ 42823-46-1 ]
4-Guanidino-benzoic acid 4-[4-(3,4,5-trimethoxy-benzyl)-piperazine-1-carbonyl]-phenyl ester; compound with methanesulfonic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

57
[ 42823-46-1 ]
C₂₅H₃₀N₆O₆*CH₄O₃S [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

58
[ 42823-46-1 ]
C₂₇H₃₄N₆O₆*CH₄O₃S [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 895 - 899

59
[ 42823-46-1 ]
[ 58582-30-2 ]
4-[9-chloro-7-(2-fluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		4-[9-Chloro-7-(2-fluoro-phenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-benzoic acid (I-52) Method Q: A solution of 8-chloro-4-dimethylaminomethylene-1-(2-fluoro-phenyl)-3,4-dihydro-benzo[c]azepin-5-one (5k) (0.22 g, 0.64 mmol), 4-guanidino-benzoic acid hydrochloride (0.15 g, 0.70 mmol) and diisopropylethylamine (i-Pr2EtN) (0.23 mL, 1.32 mmol) in DMF (2.5 mL) was submitted to microwave irradiation (300 W) for 300 sec at 250 C. The mixture was cooled and then poured into H2O (100 mL). While stirring, 1N HCl was added dropwise to pH=3 followed by EtOAc (50 mL). The resulting precipitate was collected by filtration and dried under vacuum to yield I-52 as a tan solid (0.13 g, 47%).

Reference： [1]Patent: US2005/256102,2005,A1 .Location in patent: Page/Page column 145

60
(E)-8-chloro-1-(2,6-difluorophenyl)-4-((dimethylamino)methylene)-3H-benzo[c]azepin-5(4H)-one [ No CAS ]
[ 42823-46-1 ]
[ 869363-13-3 ]

Yield	Reaction Conditions	Operation in experiment
42%		4-[9-Chloro-7-(2,6-difluoro-phenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-benzoic acid (I-135) Method R: 8-Chloro-4-dimethylaminomethylene-1-(2,6-difluoro-phenyl)-3,4-dihydro-benzo[c]azepin-5-one (5aa) (2.6 g, 7.1 mmol), 4-guanidino-benzoic acid hydrochloride (1.7 g, 7.8 mmol) and K2CO3.1.5H2O (2.6 g, 15.6 mmol) in EtOH (50 mL) were refluxed for 14 h. The mixture was cooled and then poured into H2O (400 mL). While stirring, 1N HCl was added dropwise to pH=3. EtOAc (400 mL) was then added and the organic portion was washed with H2O (2×100 mL), dried over Na2SO4 and concentrated to dryness in vacuo. The residue was suspended in CH2Cl2 and filtered. The solids were dissolved in EtOAc, filtered through silica gel, concentrated to dryness in vacuo and dried under vacuum to yield 1-135 as a white solid (1.4 g, 42%).

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 6598 - 6603
[2]Patent: US2005/256102,2005,A1 .Location in patent: Page/Page column 145

Yield	Reaction Conditions	Operation in experiment
67%		4-Guanidino benzoic acid hydrochloride 2N NaOH solution 36 mL was added to a solution of methyl isothiourea disulfate 10.0 g (0.07 mol) in 36 mL water with cooling in ice bath, and stirred, then 9.5 g (0.069 mol) 4-aminomethylbenzoic acid in 2N NaOH solution 70 mL was added dropwise. The mixture was left to stand overnight at room temperature and then chilled in ice water for 1 hr. The precipitated white crystals were filtered off and washed with cold water. The filtrate was dissolve in warm 1N HCl and insoluble material was removed by filtration. The solution was concentrated in vacuum to crystallize. The colorless prisms crystallized when the solution was cooled, then filtered and dried, gave 4-guanidinobenzoic acid hydrochloride 10.0 g (yield 67%). LC/MS=180(M+H)

62
hydrochloric acid-dioxane [ No CAS ]
[ 178262-20-9 ]
[ 42823-46-1 ]
[ 144-55-8 ]
[ 775263-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In N,N-dimethyl-formamide;	EXAMPLE 37 Synthesis of ethyl 7-[(4-guanidinobenzoyl)amino]-1,2,3,4-tetrahydronaphthalene-2-acetate (Compound No. 95) hydrochloride In 20 ml of N,N-dimethylformamide, 0.63 g of <strong>[42823-46-1]4-guanidinobenzoic acid hydrochloride</strong> and 0.79 g of ethyl 7-amino-1,2,3,4-tetrahydronaphthalene-2-acetate hydrochloride were dissolved. To the solution, 0.036 g of 4-dimethylaminopyridine, 0.41 ml of triethylamine and 0.64 g of dicyclohexylcarbodimide were added with cooling and stirred overnight at room temperature. The precipitate was filtered and the solvent was distilled off under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the concentrated residue thus obtained and precipitated product was filtered. The precipitated product was converted to hydrochloride by treating with a hydrochloric acid-dioxane solution to yield 0.5 g of the entitled compound. mp:100 C. (decomposed) 1 H-NMR(270 MHz,DMSO-d6) delta ppm:10.15-10.04(m,2H),8.05-8.02(m,2H), 7.68-7.34(m,7H),7.05-7.02(m,1H),4.11(q,2H,J=7.34 Hz), 2.85-2.74(m,3H),2.49-2.35(m,3H),2.28-2.13(m,1H),1.91-1.78(m,1H), 1.49-1.38(m,1H),1.21(t,3H,J=7.3 Hz)

Reference： [1]Patent: US5629321,1997,A

63
[ 884196-37-6 ]
[ 42823-46-1 ]
4-(9-chloro-5-methyl-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%	With potassium carbonate; In ethanol; at 140℃; for 0.166667h;Irradiation;	8-Chloro-4-dimethylamino-methylene-3-methyl-3/4-dihydro-2H- benzo[fr]azepine-2,5-dione (v-i) (0.125 g, 0.45 mmol) was dissolved in ethanol (5 mL), then 4-guanidinebenzoic acid hydrochloride (0.116 g, 0.54 mmol) and potassium carbonate (0.153 g, 1.08 mmol) were added. The mixture was heated to 140 0C in a microwave reactor for 10 minutes, after which it was poured into water (10 mL). Using IM aqueous HCl, the mixture was acidified to pH 4. The solid was filtered and washed with water and diethyl ether, then dried under reduced pressure at 40 0C for 16 h to give 1-69 (5% yield) after purification by C-18 RP LC-MS chromatography: HRMS Calcd. for C20H15ClN4O3: 395.0910, Found 395.0938.

Reference： [1]Patent: WO2006/41773,2006,A2 .Location in patent: Page/Page column 318

64
[ 150-13-0 ]
[ 42823-46-1 ]

Yield	Reaction Conditions	Operation in experiment
		A. 4-guanidinobenzoic acid hydrochloride was prepared from 4-aminobenzoic acid in a manner similar to that of Example 3A.

Reference： [1]Patent: US5086069,1992,A

65
[ 16060-65-4 ]
[ 42823-46-1 ]
4-guanidinobenzoic acid methyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In methanol;	EXAMPLE 5 4-[[4-(4-Pyridinyl)-2-pyrimidinyl]amino]benzoic acid, methyl ester A solution of 10.0 g of 4-guanidinobenzoic acid, hydrochloride in 310 ml of methanol was mixed with 6.0 ml (9.68 g) of thionyl chloride at 0 C. for 15 minutes, then stirred for one hour at room temperature and then heated at reflux for 16 hours. The solvent ws removed in vacuo and the solid was washed with ether and air dried to give 11.4 g of white crystals (A). The above procedure was repeated using 20.0 g of 4-guanidinobenzoic acid, 11.9 ml (19.4 g) of thionyl chloride and 600 ml of methanol to give 22.6 g of white crystals (B). The products (A) and (B) were combined and recrystallized from absolute ethanol. The product was washed with cold absolute ethanol and air dried giving 26.2 g of p-guanidinobenzoic acid, methyl ester, hydrochloride as white crystals, mp 137-138.5 C. (dec.).

Reference： [1]Patent: US4788195,1988,A

66
[ 110-54-3 ]
[ 42823-46-1 ]
[ 7035-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;	STR40 Method A To 100 ml of thionyl chloride, was added 21.6 g of <strong>[42823-46-1]4-guanidinobenzoic acid hydrochloride</strong>. The mixture was heated with stirring under reflux for one hour. n-Hexane was added to the reaction mixture to obtain pale yellow crystals of 4-guanidinobenzoyl chloride hydrochloride.

Reference： [1]Patent: US4454338,1984,A

67
1-(3-dimethylaminoproyl)-3-ethylcarbodiimide hydrochloride [ No CAS ]
3-(2-aminoethoxy)benzamidine dihydrochloride [ No CAS ]
[ 42823-46-1 ]
N-[2-(3-amidinophenoxy)ethyl]-4-guanidinobenzamide bistrifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; triethylamine; In N-methyl-acetamide;	Step 4 Synthesis of N-[2-(3-amidinophenoxy)ethyl]-4-guanidinobenzamide bistrifluoroacetate: 152 mg (0.7 mmol) of <strong>[42823-46-1]4-guanidinobenzoic acid hydrochloride</strong>, 166 mg (0.66 mmol) of 3-(2-aminoethoxy)benzamidine dihydrochloride, 142 mg (1.4 mmol) of triethylamine, 110 mg (0.7 mmol) of 1-hydroxybenzotriazole (hydrous, 87 %) and 134 mg (0.7 mmol) of 1-(3-dimethylaminoproyl)-3-ethylcarbodiimide hydrochloride were stirred in 3 ml of dimethylformamide at room temperature overnight. The solvent was evaporated under reduced pressure, and the obtained residue was purified by the reversed-phase high-performance liquid chromatography with silica gel, containing octadodecyl group chemically bonded thereto, as the filler. After the elution with a mixed solvent of water and acetonitrile containing 0.1 % (v/v) of trifluoroacetic acid, the fraction of the intended product was freeze-dried to obtain the title compound. Yield: 172 mg (0.3 mmol) (46 %). MS (ESI, m/z) 341 (MH+) H-NMR (DMSO-d6) delta 3.65 (2H, dt), 4.20 (2H, t), 7.28-7.42 (5H, m), 7.53 (1H, t), 7.70 (4H, brs), 7.93 (2H, d), 8.78 (1H, t), 9.20 (2H, br), 9.30 (2H, br), 10.15 (1H, s).

Reference： [1]Patent: EP976722,2000,A1

68
[ 403792-85-8 ]
[ 42823-46-1 ]
[ 893554-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1-methyl-pyrrolidin-2-one; at 160℃; for 1h;Microwave irradiation;	Preparation of Intermediate (hereinafter ?Int?) 3: A mixture of Int-1 (720 mg, 4.34 mmol) and N,N-dimethylformamide dimethyl acetal (DMF.DMA) (5 mL) was heated in microwave (Emry's Optimizer) at 160 C. After 4 hours, the reaction mixture was concentrated in vacuo and hexane (100 mL) was poured. The resulting solid was filtered and washed with hexanes and dried to give Int-2. MS found for C12H19N3O (m/z): 223.1 [M++1]. A mixture of Int-2 (222 mg, 1.0 mmol), <strong>[42823-46-1]4-guanidinobenzoic acid hydrochloride</strong> (215 mg, 1.0 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.3 mL, 2.0 mmol) in N-methyl-2-pyrrolidone (NMP) (4 mL) was heated in microwave (Emry's Optimizer) at 160 C. After 1 hour, the reaction mixture was diluted with water and acetonitrile and directly purified by preparative high performance liquid chromatography (HPLC) affording Int-3. MS found for C18H19N5O2 (m/z): 338.1 [M++1].

Reference： [1]Patent: US2010/9990,2010,A1 .Location in patent: Page/Page column 31-32

69
[ 67-56-1 ]
[ 42823-46-1 ]
[ 122228-09-5 ]

Yield	Reaction Conditions	Operation in experiment
92%		To a stirred suspension of 4-aminobenzoic acid (50 g, 0.364 mole) in a mixture of concentrated HCl/water (46 mL/283 mL) was added cyanamide (35 g, 0.839 mole) at room temperature. The reaction mixture was heated at 100 C. for 6 hours. The reaction mixture was then allowed stand at room temperature (without stirring) for 16 hours. The precipitated solid was filtered and washed with water (100 mL). The solid was taken in aqueous K2CO3 solution (30 g in 400 mL of water) and stirred for 30 minutes. The solid was filtered, washed with water (2×50 mL) and dried under vacuum to provide Int-2A (35 g, 53%) as white solid. 1H NMR (200 MHz, dmso-d6): delta 8.40-8.21 (bs, 2H), 7.93 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H). Mass (m/z): 180.1 [M++1]. To a stirred suspension of Int-2A (35 g, 195.5 mmol) in methanol (350 mL) was added acetyl chloride (35 mL, 490 mmol) dropwise at 0 C. under inert atmosphere over a period of 20 minutes. The reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material (by thin layer chromatography (TLC)), the reaction mixture was neutralized using solid NaHCO3 at 0 C. Solid (excess NaHCO3) was filtered and filtrate was evaporated under vacuum to get crude compound. The crude compound was washed with EtOAc (100 mL) to afford pure Int-2B (35 g, 92%) as white solid. 1H NMR (200 MHz, dmso-d6): delta 8.45-8.23 (bs, 2H), 7.98 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.8 Hz, 2H), 3.83 (s, 3H). Mass (m/z): 194.1 [M++1].

Reference： [1]Patent: US2010/29638,2010,A1 .Location in patent: Page/Page column 62

70
C₁₇H₂₂N₄O₂ [ No CAS ]
[ 42823-46-1 ]
[ 1204526-31-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 150℃; for 0.5h;Microwave irradiation;	A solution of 4-chloro-pyridin-2-ylamine (800 mg, 6.22 mmol) and morpholine (8.1 mL, 93.34 mmol) in N-methyl-2-pyrrolidone (NMP) (2 mL) was heated in a microwave (Emry's Optimizer) at 200 C. for 10 minutes. The resulting solution was directly purified by flash chromatography (SiO2, 95:5:0.5/DCM:MeOH:NH4OH) to give 4-morpholin-4-yl-pyridin-2-ylamine (Int-1). MS found for C9H13N3O as (M+H)+ 180.39. A solution of Int-1 (418 mg, 2.34 mmol) and 3-chloro-pentane-2,4-dione (0.3 mL, 2.45 mmol) in NMP (2.5 mL) was added and heated in a microwave (Emry's Optimizer) at 150 C. for 30 minutes. The resulting solution was directly purified by flash chromatography (SiO2, 96:4:/DCM:MeOH) to give 1-(2-methyl-7-morpholin-4-yl-imidazo[1,2-a]pyridin-3-yl)-ethanone (Int-2). MS found for C14H17N3O2 as (M+H)+ 260.39. A mixture of Int-2 (293 mg, 1.13 mmol) and DMF.DMA (2.3 mL) was heated at 150 C. for 10 hours. The mixture was concentrated and used further without purification. MS found for C17H22N4O2 as (M+H)+ 315.23. A solution of 1-(2-methyl-7-morpholin-4-yl-imidazo[1,2-a]pyridin-3-yl)-ethanone (263 mg, 0.84 mmol), <strong>[42823-46-1]4-guanidinobenzoic acid hydrochloride</strong> (180 mg, 0.841) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.25 mL, 1.67 mmol) in DMF (3 mL) was heated in a microwave (Emry's Optimizer) at 150 C. for 30 minutes. The reaction mixture was then diluted with water and acetonitrile and purified by preparative HPLC affording 4-[4-(2-methyl-7-morpholin-4-yl-imidazo[1,2-a]pyridin-3-yl)-pyrimidin-2-ylamino]-benzoic acid after lyophilization. MS found for C23H22N6O3 as (M+H)+ 431.46. To the above carboxylic acid (10 mg, 0.023 mmol) in DMF (1 mL), was added O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) (13 mg, 0.034 mmol), 1,2-phenylenediamine (5 mg, 0.046 mmol), DIPEA (0.01 mL, 0.068 mmol), and stirred at room temperature for 16 hours. The reaction mixture was diluted with water and acetonitrile and directly purified by preparative HPLC affording the title compound after lyophilization. MS found for C29H28N8O2 as (M+H)+ 521.28. 1H NMR (400 MHz, dmso-d6): delta 9.54 (d, J=8.0 Hz, 1H); 8.41 (d, J=5.6 Hz, 1H); 7.90 (d, J=8.4 Hz, 2H); 7.79 (d, J=8.4 Hz, 2H); 7.11 (d, J=7.6 Hz, 1H); 7.02-6.97 (m, 2H); 6.83 (d, J=7.6 Hz, 2H); 6.71-6.67 (m, 2H); 3.76 (m, 4H); 3.29 (m, 4H); 2.58 (s, 3H).

Reference： [1]Patent: US2010/29638,2010,A1 .Location in patent: Page/Page column 79

71
C₁₇H₂₂N₄O₂ [ No CAS ]
[ 42823-46-1 ]
[ 1204526-37-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 140℃; for 0.166667h;Microwave irradiation;	2-amino-isonicotinic acid methyl ester (500 mg, 3.28 mmol) was dissolved in NMP (5 ml). 3-chloro-pentane-2,4-dione (0.42 ml, 1.5 eq) was added and the reaction mixture was heated in a microwave at 125 C. for 10 minutes. The reaction mixture was then diluted with saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic phase was dried with MgSO4 and evaporated. The solids were purified by silica gel chromatography (Hex:EtOAc 1:3) to give Int-1. Int-1 (200 mg, 0.86 mmol) was suspended in DMF-DMA (5 mL) and heated in a microwave at 160 C. for 30 minutes. The solid Int-2 was filtered out and used for next step without further purification. To Int-2 (100 mg, 0.348 mmol) in DMF, 4-guanidino-benzoic acid-HCl salt (150 mg, 2.0 eq) and DBU (0.14 ml, 3 eq) was added and the mixture was heated in the a microwave at 140 C. for 10 minutes. The reaction mixture was then diluted with 1N HCl and extracted with EtOAc. The organic phase was dried and evaporated to Int-3 which was used for next step without additional purifications. Int-3 (50 mg, 0.124 mmol), benzene-1,2-diamine (23.7 mg, 2.0 eq), HOBt (16.76 mg, 1.0 eq) and triethylamine (TEA) (0.02 mL, 2.0 eq) were mixed together in NMP at room temperature to have Compound 4. The reaction mixture was diluted with EtOAc and washed with water. The organic phase was dried, evaporated and purified by reverse phase chromatography. MS found for C27H23N7O3 as (M+H)+ 494.32. 1H NMR (400 MHz, dmso-d6): delta 10.02 (s, 1H), 9.73 (d, J=7.6 Hz, 1H), 9.49 (s, 1H), 8.62 (d, J=5.2 Hz, 1H), 8.14 (s, 1H), 7.94-7.85 (m, 4H), 7.40 (dd, J=7.2, 5.6 Hz, 1H), 7.21 (d, J=5.6 Hz, 1H), 7.12 (d, J=7.6 Hz, 1H), 6.93 (dd, J=8.0, 1.6 Hz, 1H), 6.74 (d, J=8.0 Hz, 1H), 6.55 (d, J=8.0 Hz, 1H), 4.82 (s, 2H), 3.87 (s, 3H), 2.67 (s, 3H).

Reference： [1]Patent: US2010/29638,2010,A1 .Location in patent: Page/Page column 81

72
[ 1204526-76-0 ]
[ 42823-46-1 ]
C₂₂H₂₁N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 170℃; for 0.333333h;Microwave irradiation;	A mixture of Int-I (2.00 g, 0.012 mol), 2-methoxylethanol (10 mL), KOtBu (2.59 g, 0.023 mol) and Cu (dendritic, 3u, 2.86 g) was heated under microwave condition with stirring at 180 C. for 3 hours. The solids were filtered and filtrate was concentrated, and purified with silica gel chromatography (5% MeOH/DCM) to afford Compound J (0.88 g, 45%). MS m/z: 169 (MH+). A mixture of Int-J (0.88 g, 5.2 mmol) and Int-K (0.59 mL, 5.2 mmol) in NMP (6 mL) was heated under microwave condition at 135 C. for 30 minutes. The resultant mixture was then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and dried (MgSO4). Filtration followed by concentration gave Int-L (0.96 g, 74%). MS m/z: 249 (MH+). Int-L (0.96 g, 3.9 mmol) and DMF-DMA (2 mL) in DMF (5 mL) was heated under microwave condition with stirring at 170 C. for 15 minutes. Water was then added and the precipitate formed was collected by filtration to afford Int-M (0.92 g, 78%). MS m/z: 304 (MH+). Int-M (0.92 g, 3.0 mmol), Int-N (0.65 g, 3.0 mmol) and DBU (1.25 mL, 9.1 mmol) in DMF (5 mL) was heated under microwave condition with stirring at 170 C. After 20 minutes water was added to the reaction mixture and acidified to about pH 4 with 1N HCl. The precipitate formed was collected by filtration to afford Int-O (1.98 g). MS m/z: 420 (MH+). Crude Int-O (0.25 g) was coupled with phenylenediamine (0.095 g, 0.9 mmol) in the presence of HATU (0.28 g, 0.7 mmol) and triethylamine (0.33 mL, 2.4 mmol) in DMF (2 mL) and then was purified by preparative HPLC to afford the title compound (0.033 g). MS (C28H27N7O3) m/z: 510 (MH+). NMR 1H NMR (dmso-d6): delta 9.90 (s, 1H), 9.51 (s, 1H), 9.17 (s, 1H), 8.57 (d, J=5.6 Hz, 1H), 7.94 (d, J=8.8 Hz, 2H), 7.83 (d, J=8.8 Hz, 2H), 7.53 (d, J=9.6 Hz, 1H), 7.21 (d, J=9.6 Hz, 1H), 7.12 (m, 2H), 6.94 (t, J=15.2 Hz, 1H), 6.76 (d, J=7.6 Hz, 1H), 6.58 (t, J=7.6 Hz, 1H), 4.84 (s, 2H), 3.90 (m, 2H), 3.53 (m, 2H), 3.21 (s, 3H), 2.59 (s, 3H).

Reference： [1]Patent: US2010/29638,2010,A1 .Location in patent: Page/Page column 93-94

73
[ 503-74-2 ]
Fmoc-Rink resin [ No CAS ]
[ 74124-79-1 ]
[ 42823-46-1 ]
[ 146982-27-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
[ 1315271-54-5 ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 458 - 465

74
[ 116-53-0 ]
Fmoc-Rink resin [ No CAS ]
[ 74124-79-1 ]
[ 42823-46-1 ]
[ 146982-27-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
[ 1315271-55-6 ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 458 - 465

75
Fmoc-Rink resin [ No CAS ]
[ 74124-79-1 ]
[ 557-59-5 ]
[ 42823-46-1 ]
[ 146982-27-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
[ 1315271-58-9 ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 458 - 465

76
Fmoc-Rink resin [ No CAS ]
[ 74124-79-1 ]
[ 111-14-8 ]
[ 42823-46-1 ]
[ 146982-27-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
C₂₈H₄₄N₈O₅ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 458 - 465

77
Fmoc-Rink resin [ No CAS ]
[ 74124-79-1 ]
[ 506-12-7 ]
[ 42823-46-1 ]
[ 146982-27-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
C₃₈H₆₄N₈O₅ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 458 - 465

78
Fmoc-Rink resin [ No CAS ]
[ 74124-79-1 ]
[ 42823-46-1 ]
[ 146982-27-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
C₂₁H₃₂N₈O₄ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 458 - 465

79
Fmoc-Rink resin [ No CAS ]
[ 74124-79-1 ]
[ 42823-46-1 ]
[ 146982-27-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
[ 107-92-6 ]
[ 1315271-53-4 ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 458 - 465

80
[ 67-56-1 ]
[ 42823-46-1 ]
4-guanidinobenzoic acid methyl ester hydrochloride [ No CAS ]

Reference： [1]Synlett,2013,vol. 24,p. 1663 - 1666

81
[ 24424-99-5 ]
[ 42823-46-1 ]
4-(N',N"-bis[(2-methyl-2-propanyl)oxy]carbonyl}carbamimidamido)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide; In ethanol; water; at 20℃;	Example 10: 4-(N',N"-bisi 2-methyl-2- propanyPoxy] carbony 1 } carbamimidarnido benzoic acid To a solution of <strong>[42823-46-1]4-carbamimidamidobenzoic acid hydrochloride</strong> (0.27 g, 1.3 mmol) in ethanol (10 mL), 2 M aqueous NaOH (1.0 mL) and di-tert-butyl dicarbonate (0.68 g, 3.1 mmol) were added and stirred at room temperature overnight. The reaction was concentrated and the residue purified by flash chromatography (silica gel, 20% ethyl acetate/hexanes) to afford the title compound (0.43 g, 75%) as an off-white solid. NMR (300 MHz, DMSO-<) delta 13.1 (br. s, IH), 9.05 (br. s, 2H), 7.93 (d, 2H), 7.52 (d, 2H), 1.31 (s, 9H), 1.25 (s, 9H).

Reference： [1]Patent: WO2013/174937,2013,A1 .Location in patent: Page/Page column 68

82
[ 623-00-7 ]
[ 42823-46-1 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 3565 - 3569

83
[ 1627898-15-0 ]
[ 42823-46-1 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 3565 - 3569

84
[ 42823-46-1 ]
[ 58582-30-2 ]
4-[9-chloro-7-(2-fluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoic acid [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 630 - 634

85
[ 869366-10-9 ]
[ 42823-46-1 ]
[ 869363-13-3 ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 630 - 634

86
[ 869367-33-9 ]
[ 42823-46-1 ]
4-[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoic acid [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 630 - 634

87
[ 42823-46-1 ]
[ 82957-06-0 ]
C₁₉H₁₇N₅O₂*CH₄O₃S*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap; diisopropyl-carbodiimide; at 20℃;	At room temperature25.94 g of <strong>[42823-46-1]4-guanidinobenzoic acid hydrochloride</strong> (4-GDA.HCl) was added to 207.5 ml of pyridine solvent, 18.6 ml of N, N'-diisopropylcarbodiimide (DIC) was added and reacted. to the next, to the reaction solution comprising the above reaction, 28.3 g of 6-amidino-2-naphthol methanesulfonate (6-ANL.MsOH) and 122 mg of 4-dimethylaminopyridine (DMAP) The mixture was stirred overnight at the same temperature as that of the reaction. next, methanol (MeOH) (69.3 ml) was added to the reaction mixture which had been stirred, stirred for 1 hour, filtered, Subsequently, the compound of Formula 1 purified by a purity of 99% by a further purification process, in that not dry, saturated sodium in 233.28 ml of water (H2O) and 92.73 ml for 1 hour at a temperature of 25 C bicarbonate (NaHCO3) is added slowly to a mixed solution (solvent), and the crystal precipitates and stirred, after it was filtered, using a water and acetone by washing sequentially, the compound (purity according to the general formula (2): 98.9% ) was prepared. To the next, the compound of formula (2) Without drying, after the mixture was dispersed in 72.87 ml of methanol while maintaining the temperature at room temperature,9.3 ml of methanesulfonic acid (MsOH) was slowly added, The mixture was continuously stirred until no gas was generated. Then, it was cooled to 15 DEG C, After stirring for 10 minutes at the same temperature, the resulting solid was filtered,Washed sequentially with methanol and acetone,By hot air drying at a temperature of 50C, by drying (Purity: 99.1%, yield: 62.78%) of the nafamostat mesilate according to the above formula (3).

Reference： [1]Patent: KR101595747,2016,B1 .Location in patent: Paragraph 0054; 0055

88
[ 156-62-7 ]
[ 150-13-0 ]
[ 42823-46-1 ]

Yield	Reaction Conditions	Operation in experiment
45.8%	With hydrogenchloride; In water; at 80℃; for 3h;Cooling with ice;	1) 100 mL of concentrated hydrochloric acid was added to 250 mL of a three-necked reaction flask and mechanically stirred.2) 10 g of p-aminobenzoic acid and 30 g of lime nitrogen were mixed uniformly.3) The mixture was slowly added to the reaction flask under ice-water bath and stirred into a mixture (insoluble).4) The reaction mixture was allowed to warm to 80 C for 3 hours.5) 20 g of lime nitrogen was slowly added to the reaction flask and incubated for 3 hours.6) Check whether the pH of the reaction solution is neutral.7) The reaction solution in the reaction flask was concentrated under reduced pressure at 80 C to dryness to give a dark brown solid.8) The solid was subjected to Soxhlet extraction for 3 to 4 hours using 200 mL of methyl tert-butyl ether.9) The methyl tert-butyl ether solution was added to dry anhydrous sodium sulfate.10) A solution of dried methyl tert-butyl ether was passed through the dry HCl gas at room temperature to precipitate a solid.11) The above-mentioned precipitated solid was carefully filtered and the precipitated solid was washed with an appropriate amount of methyl t-butyl ether to obtain a wet product.12) The wet product was poured into a vacuum oven at 45 C to give a solution of guanidinobenzoate (7.2 g, 45.8%).

Reference： [1]Patent: CN106543041,2017,A .Location in patent: Paragraph 0023-0037

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Code	Phrase
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H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 42823-46-1 ] {[proInfo.proName]}

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Calculated chemistry of [ 42823-46-1 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 42823-46-1 ]

[ 42823-46-1 ] Synthesis Path-Upstream 1~5

[ 42823-46-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 42823-46-1 ]

Aryls

Amines

Carboxylic Acids

Related Parent Nucleus of [ 42823-46-1 ]

Guanidines

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

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[ 42823-46-1 ]

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[ 42823-46-1 ]