Water → HCID 58169231, compound

HRID 1484982Notes

Reaction equation

HRID 1484982 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[NH:23][N:22]=3)[C:17]([Cl:30])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.B(Cl)(Cl)Cl.O.CC(=O)OCC>C(Cl)Cl>[C:26]([C:24]1[NH:23][N:22]=[C:21]([NH:20][C:18]2[C:17]([Cl:30])=[CH:16][N:15]=[C:14]([C:11]3[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=3)[N:19]=2)[CH:25]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25135Boron TrichlorideHCID 66927369HCID 66927369, compound

Product 1

HCID 58169231HCID 58169231, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-tert-butyl-5-(4-(5-tert-butyl-1H-pyrazol-3-ylamino)-5-chloropyrimidin-2-yl)thiophene-2-sulfonamide (95 mg, 0.22 mmol) and BCl3 (4 mL of 1N solution in DCM) in DCM (8 mL) was stirred for 0.5 h, After addition of water and extraction with EA (3×), the combined organic layers were dried (NaHSO4), filtered. The filtrate was concentrated to afford the title compound 5-(4-(5-tert-butyl-1H-pyrazol-3-ylamino)-5-chloropyrimidin-2-yl)thiophene-2-sulfonamide (C-236) (50 mg, 62%). LC-MS (m/z)=413 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 1.34 (s, 9H), 6.57 (s, 1H), 7.58 (d, J=4.0 Hz, 1H), 7.75 (d, J=3.6 Hz, 1H), 7.81 (s, 2H), 8.47 (s, 1H), 9.52 (s, 1H).

Workup

  1. dry with materialthe combined organic layers were dried (NaHSO4)
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c2e78d0ca1964396b6882587c340fcf8
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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