Methyl 4-(3-cyanopentan-3-yl)benzoate → Methyl 2-(5-(4-(4-(3-cyanopentan-3-yl)benzamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024478

Reaction equation

HRID 1024478 reaction equation
[C:1]([C:3]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=O)=[CH:10][CH:9]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])#[N:2].[CH3:18][CH:19]([CH3:42])[CH:20]([NH:25][C:26]([C:28]1[S:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=2)=[CH:31][N:32]=1)=[O:27])[C:21]([O:23][CH3:24])=[O:22]>>[C:1]([C:3]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:39][C:36]2[CH:37]=[CH:38][C:33]([C:30]3[S:29][C:28]([C:26]([NH:25][CH:20]([CH:19]([CH3:42])[CH3:18])[C:21]([O:23][CH3:24])=[O:22])=[O:27])=[N:32][CH:31]=3)=[CH:34][CH:35]=2)=[O:14])=[CH:16][CH:17]=1)([CH2:4][CH3:5])[CH2:6][CH3:7])#[N:2]

Participants

3

Reactant 2

HCID 67150320Methyl 4-(3-cyanopentan-3-yl)benzoate2×HCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52934136Methyl 2-(5-(4-(4-(3-cyanopentan-3-yl)benzamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

Procedure

The title compound was synthesized analogous to Example 85, using methyl 4-(3-cyanopentan-3-yl)benzoate (Intermediate 6) and intermediate 2. 1HNMR (DMSO-d6, 300 MHz) δ 10.52 (s, 1H), 8.78 (d, 1H), 8.41 (s, 1H), 8.03 (d, 2H), 7.93 (d, 2H), 7.81 (d, 2H), 7.62 (d, 2H), 4.33 (m, 1H), 3.68 (s, 3H), 2.26 (m, 1H), 2.1-2.02 (m, 4H), 0.95 (t, 6H), 0.81 (t, 6H); MS (ES+): m/z 533.2 (M+1).

Sources & evidence

ORD record
ord-ef37235f957042b9a0ea56d138298beb
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Linked notes

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