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

HRID 1484880Notes

Reaction equation

HRID 1484880 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([C:16]4[S:20][C:19]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:18][CH:17]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.Br[C:26]1N=C(NC2C=C(C3CC3)NN=2)C(C)=CN=1>>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([CH3:26])=[CH:14][N:13]=[C:12]([C:16]4[S:20][C:19]([S:21]([NH2:24])(=[O:22])=[O:23])=[CH:18][CH:17]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 509438645-[4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]pyrimidin-2-yl]thiophene-2-sulfonamideHCID 581693692-bromo-5-methyl-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine

Product 1

HCID 509433775-[4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-5-methyl-pyrimidin-2-yl]thiophene-2-sulfonamideYield 24.8%

Procedure

5-(4-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-methylpyrimidin-2-yl)thiophene-2-sulfonamide (Compound 40) (43 mg, 24.8%) was prepared following same procedure as described in Compound 50 by starting with 2-bromo-5-methyl-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine. LC-MS (m/z)=377.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 0.75-0.76 (m, 2H), 0.97-0.99 (m, 2H), 1.93-1.95 (m, 1H), 2.18 (s, 3H), 6.51 (s, 1H), 7.57 (d, J=3.6 Hz, 1H), 7.73 (d, J=3.2 Hz, 1H), 7.78 (s, 2H), 8.14 (s, 1H), 9.13 (s, 1H), 12.17 (s, 1H).

Sources & evidence

ORD record
ord-13a91da57eb344e3909bdc63d4a088b0
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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