5-[4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]pyrimidin-2-yl]thiophene-2-sulfonamide → 5-{5-chloro-4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]pyrimidin-2-yl}thiophene-2-sulfonamide
Reaction equation
Br[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)[C:5]([Cl:17])=[CH:4][N:3]=1.C1(C2NN=C(NC3C=CN=C([C:33]4[S:37][C:36]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:35][CH:34]=4)N=3)C=2)CC1>>[Cl:17][C:5]1[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)=[N:7][C:2]([C:33]2[S:37][C:36]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:35][CH:34]=2)=[N:3][CH:4]=1Participants
3
Procedure
Using 2-bromo-5-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine as starting material, following same procedure as described in Compound 50, the HCl salt of 5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 42) was prepared (92.7 mg, 33.4%). LC-MS (m/z)=397.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 0.78-0.79 (m, 2H), 1.00-1.02 (m, 2H), 1.97-1.99 (m, 1H), 6.42 (s, 1H), 7.59 (d, J=4.4 Hz, 1H), 7.78 (d, J=3.6 Hz, 1H), 7.84 (s, 2H), 8.50 (s, 1H), 9.65 (s, 1H).
Sources & evidence
- ORD record
- ord-9ce823895708485e8714e4a186623bec
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422271B2
Reaction notes
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