Pyridine → HCID 52935917, compound

HRID 1024459Notes

Reaction equation

HRID 1024459 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].[Cl:32][C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[Cl:32][C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[S:40]([NH:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[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]=2)=[CH:23][CH:24]=1)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 1049PyridineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Product 1

HCID 52935917HCID 52935917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (1.5 ml) was added to a solution of methyl-2-(4-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 3, 160 mg) in DCM (4 ml), and reaction mixture was stirred for 5 minutes. 2,4 dichloro benzenesulfonyl chloride (130 mg) was added and reaction mixture was stirred for 16 hours at RT. Organic solvent was concentrated to obtain sticky solid, was purified by column chromatography (silica gel, EtOAc-petroleum ether) to obtain title compound as solid. Yield: 215 mg (82%); 1H NMR (CDCl3, 300 MHz): δ 7.97 (d, 1H), 7.81 (d, 2H), 7.75 (d, 1H), 7.63 (s, 1H), 7.51 (d, 1H), 7.33 (dd, 1H), 7.21 (d, 2H), 7.13 (bs, 1H), 4.73 (m, 1H), 3.78 (s, 3H), 2.32 (m, 1H), 1.04 (dd, 6H); MS (ESI) m/z 542.0 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-739fc63243164bb78612e963879c3c8c
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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