118488-08-7|1-(Thiophen-3-yl)ethanamine| Ambeed

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Quality Control of [ 118488-08-7 ] Purity: 95% SDS Specification

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Product Details of [ 118488-08-7 ]

CAS No. :	118488-08-7
Formula :	C₆H₉NS
M.W :	127.21
SMILES Code :	CC(N)C1=CSC=C1
MDL No. :	MFCD08452688
InChI Key :	KXCGQPCMPZULFH-UHFFFAOYSA-N
Pubchem ID :	14249915

Safety of [ 118488-08-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301
Precautionary Statements:	P301+P310
Class:	6.1
UN#:	2810
Packing Group:	Ⅲ

Application In Synthesis of [ 118488-08-7 ]

* 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.

Downstream synthetic route of [ 118488-08-7 ]

[ 118488-08-7 ] Synthesis Path-Downstream 1~32

1
[ 118488-07-6 ]
[ 118488-08-7 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

2
[ 118488-08-7 ]
[ 6065-82-3 ]
[ 120350-33-6 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

3
[ 1468-83-3 ]
[ 118488-08-7 ]

Yield	Reaction Conditions	Operation in experiment
75%		Preparation 8 1-Thiophen-3-yl-ethylamine The synthetic procedure used in this preparation is outlined below in Scheme J. To a solution of 3-Acetylthiophene (2.0 g, 15.85 mmol) and ammonium acetate (12.2 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dicholromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 1.5 g 1-thiophen-3-yl-ethylamine, yield: 75%. MS (M+H)=128.
75%		Preparation 7: l-Thiophen-3-yl-ethylamine; The synthetic procedure used in this preparation is outlined below in Scheme I. To a solution of 3-Acetylthiophene (2.0 g, 15.85 mmol) and ammonium acetate (12.2 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 1 l.lmmol) in one portion. The reaction mixture was stirred overnight at RT. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH =13. The aqueous solution was ex- EPO <DP n="63"/>tracted with dichloromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 1.5 g l-thiophen-3-yl- ethylamine, yield: 75%. MS (M+H) = 128.
75%		The synthetic procedure used in this preparation is outlined below in Scheme I. To a solution of 3-Acetylthiophene (2.0 g, 15.85 mmol) and ammonium acetate (12.2 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dicholromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 1.5 g 1-thiophen-3-yl-ethylamine, yield: 75%. MS (M+H)=128.

75%	With ammonium acetate; sodium cyanoborohydride; In methanol; at 20.0℃;	Preparation 8 1-Thiophen-3-yl-ethylamine The synthetic procedure used in this preparation is outlined below in Scheme J. 3-Acetylthiophene (2.0 g, 15.85 mmol) and ammonium acetate (12.2 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dichloromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 1.5 g 1-thiophen-3-yl-ethylamine, yield: 75%. MS (M+H)=128.
	With ammonium acetate; sodium cyanoborohydride; In methanol; at 20.0℃; for 16.0h;	Step 1. To a solution of compound 3-1 (2 g, 15.9 mmol) in MeOH (20 mL) was added NH4OAc (12.2 g, 0.159 mol) and NaBH3CN (3.5 g, 55.5 mmol) at 20C. After the mixture was stirred at 20C for 16 h, it was concentrated. The residual was partitioned between EtOAc (50 mL) and NaOH solution (5 M, 5 mL) (adjust pH>13). The organic layer was washed with brine (20 mLx2), concentrated and purified by column (20 %-30 % MeOH in DCM) to give the crude compound 3-2 (800 mg, 40% yield). lH NMR (400 MHz, DMSO-/ ) delta 7.63 - 7.61 (d, J= 8.0 Hz, 1 H), 7.58 - 5.57 (m, 1 H), 7.25 - 7.23 (d, J= 8.0 Hz , 2 H), 4.53 - 4.48 (m, 1 H), 1.51 - 1.49 (d, J= 8.0 Hz , 3 H).

References: [1]Patent: US2008/4442,2008,A1 .Location in patent: Page/Page column 198.
[2]Patent: WO2008/55840,2008,A1 .Location in patent: Page/Page column 61-62.
[3]Patent: US2012/22067,2012,A1 .Location in patent: Page/Page column 38.
[4]Patent: US2015/191487,2015,A1 .Location in patent: Paragraph 0661-0662.
[5]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.
[6]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.
[7]Patent: WO2015/95227,2015,A2 .Location in patent: Page/Page column 80; 81.

4
[ 56423-56-4 ]
[ 118488-08-7 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

5
[ 14861-60-0 ]
[ 118488-08-7 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

6
[ 118488-08-7 ]
[ 118487-83-5 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

7
[ 118488-08-7 ]
[ 120350-44-9 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

8
[ 118488-08-7 ]
[ 120350-45-0 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

9
[ 118488-08-7 ]
[ 118487-86-8 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

10
[ 118488-08-7 ]
[ 120350-39-2 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

11
[ 118488-08-7 ]
[ 118487-84-6 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

12
[ 118488-08-7 ]
[ 118487-87-9 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

13
[ 118488-08-7 ]
[ 118487-85-7 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

14
[ 118488-08-7 ]
[ 120350-41-6 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

15
[ 118488-08-7 ]
[ 120350-40-5 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

16
[ 118488-08-7 ]
[ 118487-97-1 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1571 - 1581.

17
[ 118488-08-7 ]
[ 127099-85-8 ]
1-(1-thien-3-yl-ethyl)-biguanide hydrochloride [ No CAS ]

References: [1]Patent: US6348435,2002,B1 .Location in patent: Page column 61.

Yield	Reaction Conditions	Operation in experiment
90%		1-(3-Thienyl)ethylamine A solution of the above azide (5.0 g, 32.6 mmol) in Et2 O (80 ml) was added to a suspension of lithium aluminum hydride (1.7 g, 44.8 mmol) in Et2 O (80 ml) under a nitrogen atmosphere at such a rate as to maintain a gentle reflux. An external heat source was applied to the reaction mixture and was heated to reflux for an additional hour. H2 O (2 ml) was added carefully to the mixture, followed by 15% NaOH in H2 O (2 ml) and H2 O (6 ml). The inorganic materials were filtered from this reaction mixture and washed with Et2 O. The combined organic filtrates were dried over MgSO4, and the solvent was removed in vacuo to give the product (3.7 g, 90% yield) as an amber oil; IR (neat) 1590, 2760-3660 and 2990 cm-1; mass spectrum m/z 127 (M+); 1 H NMR (CDCl3) delta1.42 (d, J=6 Hz, 3H, CHCH3), 1.62 (s, 2H, exchanges with D2 O, NH2), 4.20 (q, J=6 Hz, 1H, CHCH3), 7.00-7.40 (m, 3H, thiophene-H).

19
(S)-1-((1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamoyl)cyclobutanecarboxylic acid [ No CAS ]
[ 118488-08-7 ]
C₂₅H₃₃N₅O₅S [ No CAS ]
C₂₅H₃₃N₅O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h;	Step 2. To a solution of compound 3-3 (500 mg, 1.23 mmol) in DMF (3 mL) was added compound 3-2 (600 mg, 4.7 mmol), DIPEA (0.5 mL, 3 mmol) and HATU (740 mg, 2 mmol) at 20C. After the mixture was stirred at 20C for 2 h, it was purified by prep-HPLC to give 3-4 (360 mg, 57% yield). Compound 3-4 (300 mg) was separated by SFC separation to give 2 isomers 3-4A and 3-4B. NMR (400 MHz, DMSO-/ ) delta 10.03 (s, 1 H), 8.12 - 8.10 (m, 1H), 7.9 -7.75 (m, 1 H), 7.55 - 7.52 (m, 2 H), 7.45 - 7.35 (m, 2 H), 7.3 - 7.2 (m, 3 H), 7.04 (m, 1 H), 6.0 (m, 1 H), 5.5 - 5.2 (m, 2 H), 5.1 - 5.0 (m, 1 H), 4.45 - 4.35 (m, 3 H), 3.1 - 2.9 (m, 4 H), 2.43 - 2.39 (m, 4 H), 1.8 - 1.7 (m, 3 H), 1.7 - 1.5 (m, 1 H), 1.5-1.33 (m, 5 H).

References: [1]Patent: WO2015/95227,2015,A2 .Location in patent: Page/Page column 80; 81.
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

20
(S)-1-((1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamoyl)cyclobutanecarboxylic acid [ No CAS ]
[ 118488-08-7 ]
1-ethyl-6-fluoro-4-oxo-7-(4-(((4-((S)-2-(1-(((S)-1-(thiophen-3-yl)ethyl)carbamoyl)cyclobutane-1-carboxamido)-5-ureidopentanamido)benzyl)oxy)carbonyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]

References: [1]Patent: WO2015/95227,2015,A2 .

21
1-(2,5-dioxopyrrolidin-1-yl) 1-ethyl cyclobutane-1,1-dicarboxylate [ No CAS ]
[ 118488-08-7 ]
C₁₄H₁₉NO₃S [ No CAS ]
C₁₄H₁₉NO₃S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

22
[ 118488-08-7 ]
C₃₂H₃₆N₆O₉S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

23
[ 118488-08-7 ]
C₃₂H₃₆N₆O₉S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

24
[ 118488-08-7 ]
C₁₂H₁₅NO₃S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

25
[ 118488-08-7 ]
C₁₆H₁₈N₂O₅S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

26
[ 118488-08-7 ]
C₂₂H₃₃N₃O₆S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

27
[ 118488-08-7 ]
C₂₂H₃₄N₄O₅S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

28
[ 118488-08-7 ]
C₂₂H₃₂N₄O₄S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

29
[ 118488-08-7 ]
C₁₇H₂₄N₄O₂S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

30
[ 118488-08-7 ]
1-ethyl-6-fluoro-4-oxo-7-(4-(((4-((S)-2-(1-(((R)-1-(thiophen-3-yl)ethyl)carbamoyl)cyclobutane-1-carboxamido)-5-ureidopentanamido)benzyl)oxy)carbonyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

31
[ 118488-08-7 ]
1-ethyl-6-fluoro-4-oxo-7-(4-(((4-((S)-2-(1-(((S)-1-(thiophen-3-yl)ethyl)carbamoyl)cyclobutane-1-carboxamido)-5-ureidopentanamido)benzyl)oxy)carbonyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

32
[ 118488-08-7 ]
N'-((S)-1-cyano-4-ureidobutyl)-N-((S)-1-(thiophen-3-yl)ethyl)cyclobutane-1,1-dicarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 989 - 1000.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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Code	Phrase
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P321
P322
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P378
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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P401
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P411
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
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

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CAS No.: 118488-08-7

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CAS No.: 118488-08-7

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[ 118488-08-7 ] Synthesis Path-Downstream 1~32

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