4-Bromo-2-fluorophenyl isocyanate → 1,1-dimethylethyl (3S)-3-[2-(2-{[(4-bromo-2-fluorophenyl)amino]carbonyl}hydrazino)-2-oxoethyl]-1-pyrrolidinecarboxylate

HRID 525155Notes

Reaction equation

HRID 525155 reaction equation
[NH:1]([C:3](=[O:17])[CH2:4][C@@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)[NH2:2].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[C:21]([F:28])[CH:20]=1>ClCCl>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:2][NH:1][C:3](=[O:17])[CH2:4][C@@H:5]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:6]2)=[O:27])=[C:21]([F:28])[CH:20]=1

Participants

4

Reactant 2

HCID 27333654-Bromo-2-fluorophenyl isocyanateHCID 866748261,1-dimethylethyl (3S)-3-(2-hydrazino-2-oxoethyl)-1-pyrrolidinecarboxylate

Product 1

HCID 866748271,1-dimethylethyl (3S)-3-[2-(2-{[(4-bromo-2-fluorophenyl)amino]carbonyl}hydrazino)-2-oxoethyl]-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl (3S)-3-(2-hydrazino-2-oxoethyl)-1-pyrrolidinecarboxylate (6.58 mmol) in dichloromethane (15 mL) was cooled to 0° C. and was treated drop-wise with 4-bromo-2-fluoro-1-isocyanatobenzene (6.58 mmol). The reaction was allowed to warm to room temperature, and after ˜30 min a white solid had formed. The reaction contents were concentrated to dryness in vacuo. No further purification was carried out on the resulting white solid (3.01 grams, 100%). MS(ES)+ m/e 459/461 [M+H]+ (bromide isotope pattern).

Workup

  1. customafter ˜30 min a white solid had formed
  2. customThe reaction contents
  3. concentrationwere concentrated to dryness in vacuo
  4. customNo further purification

Sources & evidence

ORD record
ord-8ae51a9469ea466486adf045093e2686
Source dataset
uspto-grants-2016_05
Patent number
US09340529B2

Reaction notes

Loading…