Boron Trichloride → HCID 50942863, compound

HRID 1484895Notes

Reaction equation

HRID 1484895 reaction equation
C([NH:5][S:6]([C:9]1[O:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH:26]4[CH2:28][CH2:27]4)[NH:23][N:22]=3)[C:17]([Cl:29])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:29][C:17]1[C:18]([NH:20][C:21]2[CH:25]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[NH:23][N:22]=2)=[N:19][C:14]([C:11]2[O:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:13][CH:12]=2)=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 58169492HCID 58169492, compound

Product 1

HCID 50942863HCID 50942863, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound N-tert-butyl-5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)furan-2-sulfonamide (45 mg, 0.10 mmol, 1.0 equiv.) in CH2Cl2 (5 mL) was added BCl3 (1.0 mL, 1.0 mmol, 10.0 equiv.) at room temperature. The mixture was stirred for 2 hours, then, concentrated. The residue was recrystallized with methanol and isopropylether to give the title compound 5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)furan-2-sulfonamide (Compound 240) (20 mg, 53%). LC-MS (m/z)=380.9 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.73-0.81 (m, 2H), 0.91-1.00 (m, 2H), 1.91-1.97 (m, 1H), 6.50 (s, 1H), 7.12 (d, J=3.2 Hz, 1H), 7.21 (d, J=2.8 Hz, 1H), 7.93 (s, 2H), 8.48 (s, 1H), 9.44 (s, 1H), 12.28 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was recrystallized with methanol and isopropylether

Sources & evidence

ORD record
ord-5c45158f808a4f288cb68dac2c4470f5
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

Loading…