Pyridine → HCID 52934822, compound

HRID 1024447Notes

Reaction equation

HRID 1024447 reaction equation
N1C=CC=CC=1.[CH3:7][CH:8]([CH3:31])[CH:9]([NH:14][C:15]([C:17]1[S:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[CH:20][N:21]=1)=[O:16])[C:10]([O:12][CH3:13])=[O:11].[C:32]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[C:32]([C:36]1[CH:37]=[CH:38][C:39]([C:40]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([C:19]3[S:18][C:17]([C:15]([NH:14][CH:9]([CH:8]([CH3:31])[CH3:7])[C:10]([O:12][CH3:13])=[O:11])=[O:16])=[N:21][CH:20]=3)=[CH:23][CH:24]=2)=[O:41])=[CH:43][CH:44]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Product 1

HCID 52934822HCID 52934822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.11 ml) was added to a solution of methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 150 mg) in DCM (3 ml) and the reaction mixture was stirred for 5 minutes. 4-tert-butylbenzoyl chloride (0.125 ml) was then added and the reaction mixture was stirred for 1 h. The reaction mass was quenched with water. The organic layer was dried over Na2SO4 and evaporated under reduced pressure to get dark brown solid which was purified by silica gel column chromatography (EtOAc:CHCl3, 2:8) to get off white solid. The solid was crystallized in CHCl3/pet ether to give the title compound. Yield: 160 mg (72%) white solid. 1HNMR (DMSO-d6, 300 MHz): δ 10.38 (s, 1H), 8.76 (d, 1H), 8.41 (s, 1H), 7.94 (d, 2H), 7.91 (d, 2H), 7.8 (d, 2H), 7.58 (d, 2H), 4.33 (m, 1H), 3.69 (s, 3H), 2.27 (m, 1H), 0.95 (d, 6H); MS (ES+): m/z 494 (M+1).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. customThe reaction mass was quenched with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated under reduced pressure
  5. customto get dark brown solid which
  6. customwas purified by silica gel column chromatography (EtOAc:CHCl3, 2:8)
  7. customto get off white solid
  8. customThe solid was crystallized in CHCl3/pet ether

Sources & evidence

ORD record
ord-f62644aa1e9a4b5daa7c54968bd396b9
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

Loading…