Diisopropylethylamine → 2-{[(4-Cyano-2-methoxycarbonyl-benzyl)-(1-pyridin-2-yl-ethyl)amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester

HRID 251254Notes

Reaction equation

HRID 251254 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[CH2:12]Br.[C:15]([O:19][C:20]([N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][CH:23]1[CH2:31][NH:32][CH:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)[CH3:34])=[O:21])([CH3:18])([CH3:17])[CH3:16].CCN(C(C)C)C(C)C>CC#N.CN(C1C=CN=CC=1)C>[C:15]([O:19][C:20]([N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[CH2:31][N:32]([CH2:12][C:5]1[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:14])[CH:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)[CH3:34])=[O:21])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 17965928Methyl 2-(bromomethyl)-5-cyanobenzoateHCID 672726842-[(1-Pyridin-2-yl-ethylamino)-methyl]-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 672721472-{[(4-Cyano-2-methoxycarbonyl-benzyl)-(1-pyridin-2-yl-ethyl)amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Using General Procedure A: Reaction of 2-bromomethyl-5-cyano-benzoic acid methyl ester and 2-[(1-pyridin-2-yl-ethylamino)-methyl]-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester in CH3CN with DIPEA, KI, and DMAP gave 2-{[(4-cyano-2-methoxycarbonyl-benzyl)-(1-pyridin-2-yl-ethyl)-amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester as a light yellow solid. 1H NMR (CDCl3) δ 1.56-1.59 (m, 3H), 1.71 (s, 9H), 3.86 (s, 3H), 4.23 (s, 1H), 4.28-4.30 (m, 2H), 4.40-4.47 (m, 2H), 7.10-7.16 (m, 1H), 7.24-7.32 (m, 3H), 7.42-7.46 (m, 1H), 7.51-7.66 (m, 2H), 7.71-7.76 (m, 1H), 7.82 (d, 1H, J=1.7 Hz), 7.92 (d, 1H, J=8.0 Hz), 8.53 (d, 1H, J=4.8 Hz).

Sources & evidence

ORD record
ord-4434f28de54946e58c1324cf40c4a031
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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