Boron Trichloride → HCID 178514705, compound

HRID 1484856Notes

Reaction equation

HRID 1484856 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:20]=[C:19]([NH:21][C:22]3[NH:26][N:25]=[C:24]([CH:27]4[CH2:29][CH2:28]4)[CH:23]=3)[C:18]([OH:30])=[CH:17][N:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[CH:27]1([C:24]2[CH:23]=[C:22]([NH:21][C:19]3[C:18]([OH:30])=[CH:17][N:16]=[C:15]([C:11]4[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=4)[N:20]=3)[NH:26][N:25]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 178449978HCID 178449978, compound2×

Product 1

HCID 178514705HCID 178514705, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-3-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-hydroxypyrimidin-2-yl)benzenesulfonamide (Compound 102) (25 mg, 0.053 mmol, 1.0 equiv.) in CH2Cl2 (5 mL) was added BCl3 (1.5 mL, 1.48 mmol, 28.0 equiv.) at room temperature. The mixture was stirred for 0.5 hours, then, concentrated. The residue was recrystallized with methanol and isopropyl ether to give 3-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-hydroxypyrimidin-2-yl)benzenesulfonamide (Compound 99) (20 mg, 92%). LC-MS (m/z)=373.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.75-0.83 (m, 2H), 0.92-0.99 (m, 2H), 1.87-1.99 (m, 1H), 6.47 (s, 1H), 7.47 (s, 2H), 7.76 (dd, J=8.0 Hz, 8.0 Hz, 1H), 7.95-7.98 (m, 2H), 7.76 (d, J=8.0 Hz, 1H), 8.67 (s, 1H), 9.88 (bs, 1H), 11.54 (bs, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was recrystallized with methanol and isopropyl ether

Sources & evidence

ORD record
ord-09a3a9a7baac47eb8a5259df74ec02d9
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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