Benzyl Bromide → HCID 67150311, compound

HRID 1024479Notes

Reaction equation

HRID 1024479 reaction equation
[CH3:1][CH:2]([CH3:25])[CH:3]([NH:8][C:9]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH2:33]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[S:12][C:11]([C:9]([NH:8][CH:3]([CH:2]([CH3:25])[CH3:1])[C:4]([O:6][CH3:7])=[O:5])=[O:10])=[N:15][CH:14]=2)=[CH:17][CH:18]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Product 1

HCID 67150311HCID 67150311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 200 mg) in DCM (6 ml) was added triethyl amine (0.417 ml, 5.0 equiv.) and benzyl bromide (308 mg, 3.0 eq) and the reaction mixture was stirred for 2 days at RT. The solvent was evaporated and the residue was purified by column chromatography using 1% ethylacetate in chloroform to give the title compound. Yield: 50 mg (20%). 1H NMR (CDCl3; 300 MHz): δ 7.87 (s, 1H), 7.66 (d, 1H), 7.44 (d, 2H), 7.38 (m, 5H), 7.32 (m, 1H), 6.68 (d, 2H), 4.74 (m, 1H), 4.40 (s, 2H), 3.79 (s, 3H), 2.34 (m, 1H), 1.05 (t, 6H); MS (ESI) m/z 424.2 [M+H]+, 446.1 [M+Na]+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ce088569096745888eaa5a0f8a65eee0
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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