Boron Trichloride → HCID 50944029, compound

HRID 1484955Notes

Reaction equation

HRID 1484955 reaction equation
C([NH:5][S:6]([C:9]1[S:13][C:12]([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]([C:29]([OH:31])=[O:30])=[CH:16][N:15]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[CH:26]1([C:24]2[NH:23][N:22]=[C:21]([NH:20][C:18]3[C:17]([C:29]([OH:31])=[O:30])=[CH:16][N:15]=[C:14]([C:12]4[S:13][C:9]([S:6](=[O:8])(=[O:7])[NH2:5])=[CH:10][CH:11]=4)[N:19]=3)[CH:25]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 58169460HCID 58169460, compound

Product 1

HCID 50944029HCID 50944029, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-(N-tert-butylsulfamoyl)thiophen-2-yl)-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-5-carboxylic acid (80 mg, 0.17 mmol, 1.0 eq) in CH2Cl2 (20 mL) was added 1N BCl3 (3.4 mL, 3.4 mmol, 20.0 eq) at rt. The mixture was stirred for 3 h and concentrated. The residue was purified by recrystallization with methanol and isopropylether to 4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-(5-sulfamoylthiophen-2-yl)pyrimidine-5-carboxylic acid (Compound 179) (30 mg, 44%). LC-MS (m/z)=407.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.77-0.80 (m, 2H), 0.98-1.03 (m, 2H), 1.95-2.00 (m, 1H), 6.60 (s, 1H), 7.65 (d, J=4.0 Hz, 1H), 7.92 (s, 2H), 7.95 (d, J=4.0 Hz, 1H), 8.92 (s, 1H), 10.74 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by recrystallization with methanol and isopropylether to 4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-(5-sulfamoylthiophen-2-yl)pyrimidine-5-carboxylic acid (Compound 179) (30 mg, 44%)

Sources & evidence

ORD record
ord-5b317c4c0c694041a0f93a1ecc81b390
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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