Water → 5-[4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]pyrimidin-2-yl]thiophene-2-sulfonamide

HRID 1484878Notes

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

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (300 mg, 0.717 mmol, 1.0 eq), BCl3/CH2Cl2 (7.17 ml, 7.17 mmol, 10 eq. 1 M) in CH2Cl2 (20 ml) was stirred at 20° C. under a nitrogen atmosphere for 6 h. Water (50 ml) was added into the mixture. The mixture was extracted by EA (3×50 ml). The combined organic phases were washed (sat NaHCO3), brine, dried (Na2SO4), filtered and concentrated. The residue was purified by recrystallization (solvent: EA/PE and DIPE) to afford title compound 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 50) (50.9 mg, 19.6%) as a yellow solid. LC-MS (m/z)=363.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 0.72-0.74 (m, 2H), 0.94-0.99 (m, 2H), 1.89-1.94 (m, 1H), 6.41 (s, 1H), 6.84 (s, 1H), 7.58 (d, J=4 Hz, 1H), 7.49-7.81 (m, 3H), 8.29 (d, J=5.2 Hz, 1H), 10.08 (s, 1H), 12.14 (s, 1H).

Workup

extractionThe mixture was extracted by EA (3×50 ml)
washThe combined organic phases were washed (sat NaHCO3), brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by recrystallization (solvent: EA/PE and DIPE)

Sources & evidence

ORD record: ord-ffc38c6640e34bb7a106037f930c8ab9
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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