4-Methylbenzylamine → racemic cis-2,2-Dimethyl-3-{1-(4-methylbenzyl)-6-[(5-methylpyridin-2-yl)methoxy]-1H-benzimidazol-2-yl}cyclopropanecarboxylic acid

HRID 1848738Notes

Reaction equation

CC1C=CC(CN)=CC=1.[CH3:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][NH:16][C:17]2[C:18]([NH2:32])=[CH:19][CH:20]=[C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=3)[CH:22]=2)=[CH:13][CH:12]=1.[CH3:35][C:36]1([CH3:44])[C@@H:41]2[C@H:37]1[C:38](=[O:43])[O:39][C:40]2=O>>[CH3:35][C:36]1([CH3:44])[C@H:41]([C:40]2[N:16]([CH2:15][C:14]3[CH:13]=[CH:12][C:11]([CH3:10])=[CH:34][CH:33]=3)[C:17]3[CH:22]=[C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=4)[CH:20]=[CH:19][C:18]=3[N:32]=2)[C@@H:37]1[C:38]([OH:43])=[O:39]

Participants

Reactant 3

HCID 660354-Methylbenzylamine

HCID 12851675HCID 12851675, compound

HCID 131732440N1-(4-methylbenzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamine

Product 1

HCID 90410789racemic cis-2,2-Dimethyl-3-{1-(4-methylbenzyl)-6-[(5-methylpyridin-2-yl)methoxy]-1H-benzimidazol-2-yl}cyclopropanecarboxylic acid

Procedure

The title compound was prepared using analogous conditions described for Example 1 using p-tolylmethanamine in Step A then for Intermediate I using N1-(4-methylbenzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamine and cis-6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione followed by the hydrolysis according to Example 111. MS (ESI): mass calcd. for C28H29N3O3, 455.22; m/z found, 456.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 7.58 (d, J=8.9, 1H), 7.54-7.48 (m, 1H), 7.40 (d, J=7.9, 1H), 7.13 (d, J=7.9, 2H), 7.04 (dd, J=8.8, 2.3, 1H), 6.98-6.87 (m, 3H), 5.31 (d, J=16.5, 1H), 5.24 (d, J=16.6, 1H), 5.18 (s, 2H), 2.34 (s, 6H), 2.28 (d, J=8.2, 1H), 2.07 (d, J=8.2, 1H), 1.21 (s, 3H), 0.98 (s, 3H).

Sources & evidence

ORD record: ord-0e1d9e09c6a9477a98fa571d8a174880
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952177B2

Reaction notes

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