Diisopropylethylamine → HCID 21985168, compound

HRID 1157920Notes

Reaction equation

HRID 1157920 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][NH:18][CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.Br[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:52]#[N:53])=[CH:42][CH:41]=1>CC#N>[NH2:53][CH2:52][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[C:43]1[CH:44]=[CH:45][C:40]([CH2:39][N:18]([CH2:17][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH:19]2[C:28]3[N:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:22][CH2:21][CH2:20]2)=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 219850812-[(5,6,7,8-Tetrahydroquinolin-8-ylamino)-methyl]-benzimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 21985168HCID 21985168, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the general alkylation procedure: To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.194 g, 0.51 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.30 mL, 1.72 mmol) followed by 4′-bromomethyl-2-cyanobiphenyl (0.303 g, 1.11 mmol) and the resultant mixture heated to 60° C. for 25 h. Purification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH) followed by radial chromatography on silica gel (2 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH) provided a tan foam (79 mg).

Workup

  1. customPurification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-4e957fe554f84c6cab95fb9d32b6d94c
Source dataset
uspto-grants-2010_10
Patent number
US07807694B2

Reaction notes

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