HCID 514279, compound → (E)-3-(2-{1-[(3-Cyclopentyl-1-methyl-2-pyrazin-2-yl-1H-indole-6-carbonyl)amino]cyclobutyl}-1-methyl-1H-benzimidazol-5-yl)acrylic acid

HRID 1661357Notes

Reaction equation

HRID 1661357 reaction equation
[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][C:11]([C:15](O)=[O:16])=[CH:12][CH:13]=3)[N:8]([CH3:18])[C:7]=2[C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:27][C:28](=[O:46])/[CH:29]=[CH:30]/[C:31]1[CH:45]=[CH:44][C:34]2[N:35]([CH3:43])[C:36]([C:38]3([NH2:42])[CH2:41][CH2:40][CH2:39]3)=[N:37][C:33]=2[CH:32]=1)C>>[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][C:11]([C:15]([NH:42][C:38]4([C:36]5[N:35]([CH3:43])[C:34]6[CH:44]=[CH:45][C:31](/[CH:30]=[CH:29]/[C:28]([OH:27])=[O:46])=[CH:32][C:33]=6[N:37]=5)[CH2:39][CH2:40][CH2:41]4)=[O:16])=[CH:12][CH:13]=3)[N:8]([CH3:18])[C:7]=2[C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 514279HCID 514279, compoundHCID 57835265HCID 57835265, compound

Product 1

HCID 57835349(E)-3-(2-{1-[(3-Cyclopentyl-1-methyl-2-pyrazin-2-yl-1H-indole-6-carbonyl)amino]cyclobutyl}-1-methyl-1H-benzimidazol-5-yl)acrylic acid

Procedure

3-cyclopentyl-1-methyl-2-pyrazin-2-yl-1H-indole-6-carboxylic acid 5-1 (prepared using procedures described in WO 03/010141) and (E)-3-[2-(1-aminocyclobutyl)-1-methyl-1H-benzimidazol-5-yl]acrylic acid ethyl ester 4-2 were coupled, followed by saponification of the ethyl ester, using analogous procedures to those described in Example 4 to give (E)-3-(2-{1-[(3-Cyclopentyl-1-methyl-2-pyrazin-2-yl-1H-indole-6-carbonyl)amino]cyclobutyl}-1-methyl-1H-benzimidazol-5-yl)acrylic acid 5-2 (compound 4003, Table 4).

Sources & evidence

ORD record
ord-9bb6aec70bd845dfae56e0444f33742b
Source dataset
uspto-grants-2011_10
Patent number
US08030309B2

Reaction notes

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