Furan-3-sulfonyl chloride → 1,1-Dimethylethyl [1-(5-(2-chloro-4-pyrimidinyl)-4-{2-fluoro-3-[(3-furanylsulfonyl)amino]phenyl}-1,3-thiazol-2-yl)-1-methylethyl]carbamate

HRID 239576Notes

Reaction equation

HRID 239576 reaction equation
[NH2:1][C:2]1[C:3]([F:31])=[C:4]([C:8]2[N:9]=[C:10]([C:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:22])[CH3:21])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[N:14]=2)[CH:5]=[CH:6][CH:7]=1.[O:32]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33]1>N1C=CC=CC=1>[Cl:19][C:15]1[N:14]=[C:13]([C:12]2[S:11][C:10]([C:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:22])[CH3:21])=[N:9][C:8]=2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:37]([C:34]3[CH:35]=[CH:36][O:32][CH:33]=3)(=[O:39])=[O:38])[C:3]=2[F:31])[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 22179302Furan-3-sulfonyl chloride2×HCID 579899361,1-Dimethylethyl {1-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-1-methylethyl}carbamate

Product 1

HCID 579899641,1-Dimethylethyl [1-(5-(2-chloro-4-pyrimidinyl)-4-{2-fluoro-3-[(3-furanylsulfonyl)amino]phenyl}-1,3-thiazol-2-yl)-1-methylethyl]carbamateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1,1-dimethylethyl {1-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-1-methylethyl}carbamate (400 mg, 0.862 mmol) in pyridine (50 mL) was added 3-furansulfonyl chloride (144 mg, 0.862 mmol) (in 5 cc DCM). After 4 h, 3-furansulfonyl chloride (0.20 g) was to the reaction mixture and stirred at rt overnight. The reaction mixture was concentrated in vacuo. The residue was purified via Biotage (3:1-Hex/EtOAc; 25M silica gel column) to obtain the title compound (460 mg 90% yield). MS (ESI): 594.2 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified via Biotage (3:1-Hex/EtOAc; 25M silica gel column)

Sources & evidence

ORD record
ord-c926da8107094ea584c2df5f9017f32b
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

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