1-Butanol → 3-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-ylamino)benzenesulfonamide

HRID 1484830Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.C(O)CCC>O1CCOCC1>[CH:14]1([C:12]2[CH:13]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:17][C:18]4[CH:19]=[C:20]([S:24]([NH2:27])(=[O:25])=[O:26])[CH:21]=[CH:22][CH:23]=4)[N:7]=3)[NH:10][N:11]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 95 °C

Procedure

The mixture of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (150 mg, 0.64 mmol, 1.0 equiv.), 3-aminobenzenesulfonamide (329 mg, 1.91 mmol, 3.0 equiv.), butan-1-ol (1 mL) and dioxane (0.5 mL) was stirred at 95° C. for 8 h. Then, the reaction mixture was cooled to room temperature and filtered. The residue was crystallized with methane/water/isopropyl ether to afford Compound 82 (7.7 mg, 3%). LC-MS (m/z): 372.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.62-0.63 (m, 2H), 0.88-0.92 (m, 2H), 1.82-1.86 (m, 1H), 6.06 (bs, 1H), 6.49 (bs, 1H), 7.39 (s, 2H), 7.52 (d, J=1.8 Hz, 2H), 7.97 (s, 3H), 10.02 (s, 1H), 10.45 (bs, 1H), 12.27 (bs, 1H).

Workup

temperatureThen, the reaction mixture was cooled to room temperature
filtrationfiltered
customThe residue was crystallized with methane/water/isopropyl ether

Sources & evidence

ORD record: ord-b8faf00c20544e46b57aad19e3381448
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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