Methyl 4-aminobenzoate → 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide
Reaction equation
[CH:1]1([CH2:6][C:7](Cl)=[O:8])[CH2:5]CC[CH2:2]1.[C:10]([C:12]1[CH:36]=[CH:35][C:15]([CH2:16][NH:17][C:18]2[S:19][C:20]([C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]4[N:30]([CH:32]=[CH:33][N:34]=4)[CH:31]=3)=[O:24])=[CH:21][N:22]=2)=[CH:14][CH:13]=1)#[N:11].NC1C=CC(C(OC)=O)=CC=1>>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]([C:7](=[O:8])[CH2:6][CH:1]([CH3:5])[CH3:2])[C:18]2[S:19][C:20]([C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]4[N:30]([CH:32]=[CH:33][N:34]=4)[CH:31]=3)=[O:24])=[CH:21][N:22]=2)=[CH:35][CH:36]=1)#[N:11]Participants
4
Procedure
The title compound was prepared as described in Example 52A, substituting 3-methylbutanoyl chloride for 2-cyclopentylacetyl chloride and 2-(4-cyanobenzylamino)-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ 10.75 (s, 1H), 9.62 (s, 1H), 8.43 (d, J=1.6 Hz, 1H), 8.32 (s, 1H), 8.11 (s, 1H), 7.99-7.89 (m, 2H), 7.82 (dd, J=18.8, 8.3 Hz, 2H), 7.38 (d, J=8.3 Hz, 2H), 5.63 (s, 2H), 2.14 (dt, J=13.4, 6.7 Hz, 1H), 0.88 (d, J=6.7 Hz, 6H); (APCI(+)) m/e 459 (M+H)+.
Sources & evidence
- ORD record
- ord-a08c42a3a3854ae1b16565bebf56a556
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187472B2
Reaction notes
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