[ CAS No. 102-83-0 ]

Name: 102-83-0|N1,N1-Dibutylpropane-1,3-diamine|97%
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Quality Control of [ 102-83-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 102-83-0 ]

CAS No. :	102-83-0	MDL No. :	MFCD00008219
Formula :	C₁₁H₂₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KYCGURZGBKFEQB-UHFFFAOYSA-N
M.W :	186.34	Pubchem ID :	1626
Synonyms :

Safety of [ 102-83-0 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2922
Hazard Statements:	H302-H311-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 102-83-0 ]

* 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 [ 102-83-0 ]
Downstream synthetic route of [ 102-83-0 ]

[ 102-83-0 ] Synthesis Path-Upstream 1~4

1
[ 25726-99-2 ]
[ 102-83-0 ]

Reference： [1] Journal of the Indian Chemical Society, 1946, vol. 23, p. 226
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 725,728
[3] Journal of the American Chemical Society, 1943, vol. 65, p. 2013
[4] Crisol, 1953, vol. 7, p. 19,21

2
[ 111-92-2 ]
[ 102-83-0 ]

Reference： [1] Journal of the American Chemical Society, 1943, vol. 65, p. 2013
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 725,728

3
[ 5460-29-7 ]
[ 111-92-2 ]
[ 102-83-0 ]

Reference： [1] Org.Synth.Coll., 1955, vol. Vol.III, p. 256
[2] Bulletin de la Societe Chimique de France, 1963, p. 1087 - 1090

4
[ 408353-88-8 ]
[ 102-83-0 ]

Reference： [1] Monatshefte fuer Chemie, 1981, vol. 112, p. 825 - 840

[ 102-83-0 ] Synthesis Path-Downstream 1~68

1
[ 5751-20-2 ]
[ 102-83-0 ]
2-(3-dibutylamino-propylamino)-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1946,p. 720,726

2
[ 1570-45-2 ]
[ 102-83-0 ]
isonicotinic acid-(3-dibutylamino-propylamide) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 540

3
[ 861030-95-7 ]
[ 102-83-0 ]
N⁴-(3-dibutylamino-propyl)-2,6-dimethyl-pyrimidine-4,5-diyldiamine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1947,p. 41,45

4
[ 120-57-0 ]
[ 102-83-0 ]
N,N-dibutyl-N'-piperonyl-propanediyldiamine [ No CAS ]

Reference： [1]Patent: US2851466,1955,

5
[ 50424-28-7 ]
[ 102-83-0 ]
N,N-dibutyl-N'-(6-methoxy-quinazolin-4-yl)-propanediyldiamine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1947,p. 890,894

6
[ 55496-52-1 ]
[ 102-83-0 ]
N,N-dibutyl-N'-(7-methoxy-quinazolin-4-yl)-propanediyldiamine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1947,p. 890,894

7
[ 5460-29-7 ]
[ 111-92-2 ]
[ 102-83-0 ]

Reference： [1]Organic Syntheses, Collective,1955,vol. Vol.III,p. 256
[2]Bulletin de la Societe Chimique de France,1963,p. 1087 - 1090

8
[ 25726-99-2 ]
[ 102-83-0 ]

Reference： [1]Journal of the Indian Chemical Society,1946,vol. 23,p. 226
[2]Journal of the American Chemical Society,1944,vol. 66,p. 725,728
[3]Journal of the American Chemical Society,1943,vol. 65,p. 2013
[4],1953,vol. 7,p. 19,21

9
[ 127099-85-8 ]
[ 102-83-0 ]
[ 41740-98-1 ]

Reference： [1]Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques,1969,vol. 268,p. 1407 - 1409

10
[ 105-56-6 ]
[ 102-83-0 ]
[ 15029-19-3 ]

Reference： [1]Journal of Medicinal Chemistry,1967,vol. 10,p. 165 - 171

11
[ 4122-68-3 ]
[ 102-83-0 ]
[ 6738-01-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1963,p. 1087 - 1090

12
[ 75-15-0 ]
[ 102-83-0 ]
[ 18997-73-4 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1968,vol. 18,p. 1205 - 1207

13
[ 31011-08-2 ]
[ 102-83-0 ]
[ 31011-10-6 ]

Reference： [1]Journal of medicinal chemistry,1970,vol. 13,p. 1110 - 1114

14
4-chloro-8,8-dimethyl-8,9-dihydro-furo[2,3-h]quinoline [ No CAS ]
[ 102-83-0 ]
[ 31011-16-2 ]

Reference： [1]Journal of medicinal chemistry,1970,vol. 13,p. 1110 - 1114

15
[ 31011-21-9 ]
[ 102-83-0 ]
N,N-dibutyl-N'-(2,2-dimethyl-2,3-dihydro-furo[2,3-g]quinolin-8-yl)-propane-1,3-diamine [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1970,vol. 13,p. 1110 - 1114

16
[ 31010-86-3 ]
[ 102-83-0 ]
[ 31010-88-5 ]

Reference： [1]Journal of medicinal chemistry,1970,vol. 13,p. 1110 - 1114

17
[ 14426-42-7 ]
[ 102-83-0 ]
[ 6738-01-8 ]

Reference： [1]Chimica Therapeutica,1966,vol. 1,p. 82 - 86

18
[ 23739-80-2 ]
[ 102-83-0 ]
[ 30262-30-7 ]

Reference： [1]Journal of Medicinal Chemistry,1973,vol. 16,p. 688 - 693

19
[ 55845-95-9 ]
[ 102-83-0 ]
2-[4-(4-Chloro-phenoxymethyl)-phenoxy]-N-(3-dibutylamino-propyl)-propionamide [ No CAS ]

Reference： [1]Patent: DE2731214,1979,
Chem.Abstr.,vol. 90

20
[ 3586-15-0 ]
[ 102-83-0 ]
[ 65261-24-7 ]

Reference： [1]Patent: DE2720427,1977,
Chem.Abstr.,1978,vol. 88

21
[ 102-83-0 ]
[ 25557-54-4 ]
[ 25557-58-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1970,vol. 7,p. 81 - 89

22
[ 408353-88-8 ]
[ 102-83-0 ]

Reference： [1]Monatshefte fur Chemie,1981,vol. 112,p. 825 - 840

23
[ 10328-92-4 ]
[ 102-83-0 ]
[ 158091-49-7 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1994,vol. 49,p. 788 - 800

24
[ 681246-78-6 ]
[ 102-83-0 ]
2-[(2-[3-(dibutylamino)propyl]amino}phenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3832 - 3849

25
[ 6314-28-9 ]
[ 86123-10-6 ]
[ 135944-07-9 ]
[ 102-83-0 ]
C₃₉H₄₈N₄O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

26
[ 6314-28-9 ]
[ 86123-10-6 ]
[ 102-83-0 ]
[ 214139-28-3 ]
C₃₉H₄₈N₄O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

27
[ 6314-28-9 ]
[ 35661-40-6 ]
[ 102-83-0 ]
[ 162648-54-6 ]
C₃₆H₅₀N₄O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

28
[ 6314-28-9 ]
[ 86123-10-6 ]
[ 102-83-0 ]
[ 162648-54-6 ]
C₃₆H₅₀N₄O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

29
[ 102-83-0 ]
N,N'-bis(3-N,N-dibutyl-N-methylammoniopropyl)naphthalene-1,8:4,5-bis(dicarboxamide) diiodide [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 1547 - 1558

30
[ 102-83-0 ]
[ 158091-54-4 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1994,vol. 49,p. 788 - 800

31
[ 102-83-0 ]
5,6-Benzo-2-<bis-(2-chloroethyl)amino>-3-(dibutylaminopropyl)-1-methyl-1,3,2-diazaphosphorinan-4-one [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1994,vol. 49,p. 788 - 800

32
[ 111-92-2 ]
nickel [ No CAS ]
[ 102-83-0 ]

Reference： [1]Monatshefte fur Chemie,1981,vol. 112,p. 825 - 840

33
[ 102-83-0 ]
[ 189625-05-6 ]

Reference： [1]Monatshefte fur Chemie,1981,vol. 112,p. 825 - 840

34
[ 102-83-0 ]
N-(3-Dibutylamino-propyl)-N-methyl-benzamide [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1981,vol. 112,p. 825 - 840

35
[ 111-92-2 ]
[ 102-83-0 ]

Reference： [1]Journal of the American Chemical Society,1943,vol. 65,p. 2013
[2]Journal of the American Chemical Society,1944,vol. 66,p. 725,728

36
[ 102-83-0 ]
[ 100261-32-3 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 4911,4914

37
[ 102-83-0 ]
[ 114000-58-7 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 185,187, 189

38
[ 911693-58-8 ]
[ 102-83-0 ]
3-[2-[3-(dibutylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In dichloromethane; at 20℃;	Example 64; 3-[2-[3-(dibutylamino')propyllamino}-8-(2,6-difluorophenvD-7-oxo-5,6,7,8- tetrahydropyrimido[4,5-cf]pyrimidin-4-yl1-4-methyl-N-propylbenzamide; To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfmyl)-7- oxo-5,6,7,8-tetrahydropyrimido[4,5-<f]pyrimidin-4-yl]-4-methyl-iV-propylbenzamide (30 mg, 0.06 mmol) in DCM (5 mL) was added N,iV-dibutyl-l,3-prorhoanediamine (0.06 mL, 0.26 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7]+NH4OH[3]) provided the title compound as a white solid (30 mg, 83%). LC-MS m/z 622 (M + H)+; 1H-NMR (MeOD) delta 1.00 (m, 10 H), 1.30 (m, 4 H), 1.50 (m, 9 H), 2.31 (s, 3H), 2.38 (m, 4 H), 2.48 (m, 2 H), 3.08 EPO <DP n="176"/>(m, 2 H), 4.11 (s, 2 H), 7.17 (t, 2 H), 7.46 (d, 1 H), 7.52 (m, 1 H), 7.69 (s, 1 H), 7.86 (d, 1 H).
83%	In dichloromethane; at 20℃;	To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfnyl)-7-oxo- 5,6,7,8-tetrahydropyrimido[4,5-<i]pyrimidin-4-yl]-4-methyl-lambda/-propylbenzamide (30 mg, 0.06 mmol) in DCM (5 mL) was added lambda/,lambda/-dibutyl-l,3-propanediamine (0.06 mL, 0.26 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phaseDCM/DCM[90]+MeOH[7]+NH4OH[3]) provided the title compound as a white solid (30 mg, 83%). LC-MS m/z 622 (M + H)+; 1H-NMR (MeOD) delta 1.00 (m, 10 H), 1.30 (m, 4 H), <n="158"/>1.50 (m, 9 H), 2.31 (s, 3H), 2.38 (m, 4 H), 2.48 (m, 2 H), 3.08 (m, 2 H), 4.11 (s, 2 H), 7.17 (t, 2 H), 7.46 (d, 1 H), 7.52 (m, 1 H), 7.69 (s, 1 H), 7.86 (d, 1 H).

Reference： [1]Patent: WO2006/104889,2006,A2 .Location in patent: Page/Page column 174
[2]Patent: WO2007/147109,2007,A2 .Location in patent: Page/Page column 156-157

39
[ 911693-62-4 ]
[ 102-83-0 ]
3-[2-[3-(dibutylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(1-methylethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran; at 20℃;	Example 48; 3-[2-{\|3-(dibutylammo")propyllamino}-8-(2,6-difluorophenylV7-oxo-5,6J,8- tetrahvdropyrimidor4.5-^]pyrimidin-4-yl1-4-methyl-N-(l-methylethyl)benzamide; To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7- oxo-5,6,7,8-tetrahydropyrimido[4,5-J]pyrimidin-4-yl]-4-methyl-N-(l- methylethyl)benzamide (20 mg, 0.04 mmol) in THF (3 mL) were added N5N- dibutyl-1 ,3-propanediamine (0.041 mL, 0.182 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7] +NuH4OH[3]) provided the title compound as a white solid (24 mg, 96%). LC-MS m/z 622 (M + H)+; 1H-NMR (MeOD) delta 0.98 (t, 6 H)5 1.30 (m5 10H), 1.46 (m, 4 H), EPO <DP n="167"/>1.52 (m, 2 H), 2.30 (s, 3H), 2.41 (m, 6 H), 3.07 (m, 2 H)5 4.11 (s, 2 H), 4.23 (m, 1 H), 7.15 (t, 2 H), 7.46 (d, 1 H), 7.52 (m, 1 H), 7.69 (s, 1 H), 7.85 (d, 1 H).
96%	In tetrahydrofuran; at 20℃;	To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfnyl)-7-oxo- 5,6,7,8-tetrahydropyrimido[4,5-<i]pyrimidin-4-yl]-4-methyl-lambda/-(l-methylethyl)benzamide (20 mg, 0.04 mmol) in THF (3 mL) were added lambda/,lambda/-dibutyl-l,3-propanediamine (0.041 mL, 0.182 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7] +NH4OH[3]) provided the title compound as a white solid (24 <n="150"/>mg, 96%). LC-MS m/z 622 (M + H) x++;. I 1TH-NMR (MeOD) delta 0.98 (t, 6 H), 1.30 (m, 10H), 1.46 (m, 4 H), 1.52 (m, 2 H), 2.30 (s, 3H), 2.41 (m, 6 H), 3.07 (m, 2 H), 4.11 (s, 2 H), 4.23 (m, 1 H), 7.15 (t, 2 H), 7.46 (d, 1 H), 7.52 (m, 1 H), 7.69 (s, 1 H), 7.85 (d, 1 H).

Reference： [1]Patent: WO2006/104889,2006,A2 .Location in patent: Page/Page column 165
[2]Patent: WO2007/147109,2007,A2 .Location in patent: Page/Page column 148

40
[ 911693-73-7 ]
[ 102-83-0 ]
3-[2-[3-(dibutylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N,4-dimethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 24h;	Example 171; 3-[2-{f3-(dibutylamino')propyllamino}-8-(2,6-difluoroplienylV7-oxo-5,6,7. tetrahvdropyrimidor4,5-^pyrimidin-4-yll-Lambdar,4-dimethylbenzamide; 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8- tetrahydropyrimido[4,5-cT\|pyrimidin-4-yl]-N,4-dimetliylbenzamide (0.03 g, 0.062 mmol) was dissolved in THF (5 mL) and (3-aminopropyl)dibutylamine (0.058 g, 0.31 mmol) was added. The reaction was stirred under argon for 24 h. The solvents were pumped off in vacuo, and the residue was flash chromatographed on silica gel (15 g) eluted with CH2Cl2 to 6 : 0.5 : 0.05, CH2Cl2 : ethanol : NH4OH to give the title compound as a white amorphous solid, mp 112-1150C. LC-MS m/z 594.6 (MH-H)+, 1.59 min (ret time).
	In tetrahydrofuran; for 24h;	3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5- d]pyrimidin-4-yl]-lambda/,4-dimethylbenzamide (0.03g, 0.062 mmol) was dissolved in THF (5 mL) and (3-aminopropyl)dibutylamine (0.058 g, 0.31 mmol) was added. The reaction was stirred under argon for 24 h. The solvents were pumped off in vacuo, and the residue was flash chromatographed on silica gel (15 g) eluted with CH2Cl2 to 6 : 0.5 : 0.05, CH2Cl2 : ethanol : NH4OH to give the title compound as a white amorphous solid, mp 112-1150C. LC-MS m/z 594.6 (M+H)+, 1.59 min (ret time).

Reference： [1]Patent: WO2006/104889,2006,A2 .Location in patent: Page/Page column 241
[2]Patent: WO2007/147109,2007,A2 .Location in patent: Page/Page column 219

41
[ 911693-45-3 ]
[ 102-83-0 ]
3-[2-[3-(dibutylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N-(4-fluorophenyl)-4-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In tetrahydrofuran; at 20℃;	Example 45; 3-[2-[3-(dibutylamino)propyl]amino>-8-(2,6-difluorophenyl)-7-oxo-5,6J,8- tetrahydropyrimido('4.5-o?pyrimidin-4-yll-./V-(4-fluorophenylV4-methylbenzamide; To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfmyl)-7- oxo-5,6,7,8-tetrahydropyrimido[4,5-cflpyrimidin-4-yl]-iV-(4-fluorophenyl)-4- methylbenzamide (20 mg, 0.036 mmol) in THF(3 mL) was added LambdayV-dibutyl-1,3- propanediamine (0.041 mL, 0.182 mmol). The resultant solution was stirred at room EPO <DP n="165"/>06 010792temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7] +NH4OH[3]) provided the title compound as a white solid (16 mg, 66 %). LC-MS m/z 674 (M + H)+; 1H- NMR (MeOD) delta 1.00 (t, 6H)5 1.30 (m, 4 H), 1.40 (m, 4H), 1.50 (m, 2 H), 2.34 (s, 3H), 2.43 (m, 6 H), 3.10 (m, 2 H), 4.13 (s, 2 H), 7.15 (m, 4 H), 7.53 (m, 2 H), 7.72 (m, 2 H), 7.82 (s, 1 H), 7.98 (d, 1 H).
66%	In tetrahydrofuran; at 20℃;	To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfnyl)-7-oxo- 5,6,7,8-tetrahydropyrimido[4,5-(i]pyrimidin-4-yl]-N-(4-fluorophenyl)-4-methylbenzamide (20 mg, 0.036 mmol) in THF(3 niL) was added N,7V-dibutyl- 1 ,3-propanediamine (0.041 niL, 0.182 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7] +NH4OH[3]) provided the title compound as a white solid (16 mg, 66 %). LC-MS m/z 674 (M + H)+; 1H-NMR (MeOD) delta 1.00 (t, 6H), 1.30 (m, 4 H), 1.40 (m, 4H), 1.50 (m, 2 H), 2.34 (s, 3H), 2.43 (m, 6 H), 3.10 (m, 2 H), 4.13 (s, 2 H), 7.15 (m, 4 H), 7.53 (m, 2 H), 7.72 (m, 2 H), 7.82 (s, 1 H), 7.98 (d, 1 H).

Reference： [1]Patent: WO2006/104889,2006,A2 .Location in patent: Page/Page column 163-164
[2]Patent: WO2007/147109,2007,A2 .Location in patent: Page/Page column 147

42
[ 913002-80-9 ]
[ 102-83-0 ]
[ 913002-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 120h;	Example 44 N3'-cvclopropyl-N4-[3-(dibutylamino)propyl)-5'-fluoro-6'-methyl-N2-1,3-thiazol-2-yl- 2,3'.4-biphenyltricarboxamide 3-(Dibutylamino)-1 -propylamine (60mg) was added in one portion to a stirred solution of 5'-[(cyclopropylamino)carbonyl]-3l-fluoro-2'-methyl-2-[(1 ,3- thiazol-2-ylamino)carbonyl]-4-biphenylcarboxylic acid (100 mg, 0.228 mmol), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (90 mg, 0.46 mmol), and 4-dimethylaminopyridine (10mg) in anhydrous dichloromethane (3 ml_) under an atmosphere of argon, and the resultant reaction mixture was stirred at room temperature for five days. EtOAc (15 ml) was added and the mixture washed with water (2 x 5ml), brine (5ml) then dried. Purification by flash chromatography (Si Il cartridge 4:1 to 1 :2 hexanes: EtOAc to EtOAc) afforded the title compound as a white solid (50 mg). LC-MS m/z 608 (M + H)+.

Reference： [1]Patent: WO2006/110173,2006,A2 .Location in patent: Page/Page column 91

43
[ 913002-68-3 ]
[ 102-83-0 ]
N₃'-cyclopropyl-N₂-[3-(dibutylamino)propyl]-N₄-(2,2-dimethylpropyl)-5'-fluoro-6'-methyl-2,3',4-biphenyltricarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃;	Example 64 N3'-cvclopropyl-N2-[3-(dibutylamino)propyl]-/V4-(2,2-dimethylpropyl)-5'-fluoro-6'- methyl-2.3'.4-biphenyltricarboxamide To a solution of 5'-[(Cyclopropylamino)carbonyl]-4-[(2,2-dimethylpropyl)- amino]carbonyl}-3'-fluoro-2'-methyl-2-biphenylcarboxylic acid (42.6 mg, 0.10 mmol) in DMF (2.0 mL) was added HBTU (41.7 mg, 0.11 mmol), Et3N (56.2 uL, 0.40 mmol) and Lambda/,Lambda/-dibutyl-1 ,3-propanediamine (33.8 uL, 0.15 mmol). The solution was stirred at room temperature over night. The reaction mixture was quenched with H2O (1 drop), DMSO (0.5 mL), concentrated and filtered.Purification via HPLC (Gilson) then afforded the title compound (29 mg, 48 %). LC-MS m/z 595 (M + H)+.

Reference： [1]Patent: WO2006/110173,2006,A2 .Location in patent: Page/Page column 100

Yield	Reaction Conditions	Operation in experiment
		The following compounds are exemplary of these reactive amine compounds useful in the practice of this invention. 3-Dimethylaminopropylamine, 3-Diethylaminopropylamine, 3-Dibutylaminopropylamine, 2-Dimethylaminoethylamine, 2-Diethylaminoethylamine, 2-Diisopropylaminoethylamine and 4-Diethylaminobutylamine.
		The following compounds are exemplary of these reactive amine compounds useful in the practice of this invention. 3-Dimethylaminopropylamine 3-Diethylaminopropylamine 3-Dibutylaminopropylamine 2-Dimethylaminoethylamine 2-Diethylaminoethylamine 2-Diisopropylaminoethylamine 4-Diethylaminobutylamine
		The following compounds are exemplary of these reactive amine and hydroxy compounds useful in the practice of this invention. ... 2-Dimethylaminoethanol, 3-Dibutylaminopropanol, 2-Dibutylaminoethanol, 2-Diisopropylaminoethylamine, 3-Dibutylaminopropylamine, 2-Diethylaminoethylamine, 4-Diethylamino-1-methyl-butylamine, Metanilic acid, and ...

The following compounds are exemplary of these reactive amine compounds useful in the practice of this invention. ... 2-Dimethylaminoethylamine, 4-Diethylaminobutylamine, 5-Diethylaminopentylamine, 2-Diisopropylaminoethylamine, 3-Dibutylaminopropylamine, 2-Diethylaminoethylamine, and 4-Diethylamino-1-methyl-butylamine.

45
[ 577-19-5 ]
[ 102-83-0 ]
[ 1235152-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In hydrogenchloride; water;	EXAMPLE 27 15 g. of o-nitrobromobenzene and 13 g. of <strong>[102-83-0]3-dibutylaminopropylamine</strong> are agitated with 15 g. of anhydrous sodium acetate for 7 hours at 135 C. The reaction mixture is taken up in 70 ml. of 6N hydrochloric acid and 80 ml. of water, the unreacted o-nitrobromobenzene is subjected to steam distillation, the distillation residue is rendered alkaline with potassium hydroxide solution, and extracted with ether. After distilling the residue of the ether extract, 12 g. of 2-(3-dibutylaminopropylamino)-nitrobenzene is obtained, b.p. 140-160 C. at 0.1 mm Hg.

Reference： [1]Patent: US4053472,1977,A

46
[ 455-88-9 ]
[ 102-83-0 ]
N₁-(3-dibutylaminopropyl)-2-methyl-4-nitro-1-aminobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1-methyl-pyrrolidin-2-one; at 60℃; for 15h;	Step 1: Synthesis of N-1-(3-dibutylaminopropyl)-2-methyl-4-nitro-1-aminobenzene (34) 2 g of 2-fluoro-5-nitrotoluene was added to a solution of 20 ml of N-methylpyrrolidinone, 2.88 g of <strong>[102-83-0]3-dibutylaminopropylamine</strong>, and 1.57 g of triethylamine. The reaction medium was heated at 60 C. for 15 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The reaction medium was extracted with ethyl acetate and the organic phase was then concentrated under reduced pressure. 0.74 g of N-1-(3-dibutylaminopropyl)-2-methyl-4-nitro-1-aminobenzene (34) was obtained.

Reference： [1]Patent: US2006/26773,2006,A1 .Location in patent: Page/Page column 17

47
[ 14156-91-3 ]
[ 102-83-0 ]
[ 245421-04-9 ]
[ 1091629-19-4 ]