2,3-dihydro-1H-indene-2-carbonyl chloride → Methyl 2-(5-(4-(2,3-dihydro-1H-indene-2-carboxamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024461Notes

Reaction equation

HRID 1024461 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10](Cl)=[O:11].[CH3:13][CH:14]([CH3:37])[CH:15]([NH:20][C:21]([C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=2)=[CH:26][N:27]=1)=[O:22])[C:16]([O:18][CH3:19])=[O:17]>>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([NH:34][C:31]1[CH:32]=[CH:33][C:28]([C:25]2[S:24][C:23]([C:21]([NH:20][CH:15]([CH:14]([CH3:37])[CH3:13])[C:16]([O:18][CH3:19])=[O:17])=[O:22])=[N:27][CH:26]=2)=[CH:29][CH:30]=1)=[O:11]

Participants

3

Reactant 2

HCID 213133822,3-dihydro-1H-indene-2-carbonyl chlorideHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52936140Methyl 2-(5-(4-(2,3-dihydro-1H-indene-2-carboxamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoateYield 18%

Procedure

The title compound was synthesized analogous to Example 27, using 2,3-dihydro-1H-indene-2-carbonyl chloride and intermediate 2. Yield: 18%; 1H NMR (DMSO-d6, 300 MHz): δ 10.28 (s, 1H), 8.75 (d, 1H), 8.37 (s, 1H), 7.75 (s, 4H), 7.25 (m, 2H), 7.16 (m, 2H), 4.35 (t, 1H), 3.68 (s, 3H), 3.43 (m, 1H), 3.19 (d, 4H), 2.28 (m, 1H), 0.96 (t, 6H); MS (ESI) m/z 487.0 [M+H]+.

Sources & evidence

ORD record
ord-f8d70ee0ff064d58bb019d2666f17e43
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

Loading…