Pyridine → Methyl 2-(4-(4-(4-tert-butylbenzamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024452Notes

Reaction equation

HRID 1024452 reaction equation
N1C=CC=CC=1.[CH3:7][CH:8]([CH3:31])[CH:9]([NH:14][C:15]([C:17]1[S:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)[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:20]3[N:21]=[C:17]([C:15]([NH:14][CH:9]([CH:8]([CH3:31])[CH3:7])[C:10]([O:12][CH3:13])=[O:11])=[O:16])[S:18][CH:19]=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 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Product 1

HCID 52935052Methyl 2-(4-(4-(4-tert-butylbenzamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.22 ml) was added to methyl-2-(4-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 3, 300 mg) in DCM (4 ml) and the reaction mixture was stirred for 5 minutes. 4-tert-butyl benzoyl chloride (230 mg) was added and reaction mixture was stirred for 16 hours at RT. Organic solvent was concentrated to obtain a sticky solid, which was purified by column chromatography (silica gel, EtOAc-petroleum ether) to obtain title compound as solid. Yield: 235 mg (53%). 1H NMR (DMSO-d6, 300 MHz): δ 10.31 (s, 1H), 8.83 (d, 1H), 8.36 (s, 1H), 8.10 (d, 2H), 7.91 (dd, 4H), 7.56 (d, 2H), 4.38 (t, 1H), 3.68 (s, 3H), 2.35 (m, 1H), 1.31 (s, 9H), 0.98 (t, 6H).

Workup

  1. customreaction mixture
  2. stirringwas stirred for 16 hours at RT
  3. concentrationOrganic solvent was concentrated
  4. customto obtain a sticky solid, which
  5. customwas purified by column chromatography (silica gel, EtOAc-petroleum ether)

Sources & evidence

ORD record
ord-91265a575b4a4a66b9c36e0a94741861
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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