(2S)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-ol → Ethyl (2S)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279909Notes

Reaction equation

HRID 2279909 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:54]=[CH:53][C:27]([CH2:28][P:29](=[O:52])([O:33][C@@H:34]([CH2:36][CH2:37][N:38]4[CH:42]=[C:41]([B:43]5[O:47][C:46]([CH3:49])([CH3:48])[C:45]([CH3:51])([CH3:50])[O:44]5)[CH:40]=[N:39]4)[CH3:35])[O:30][CH2:31][CH3:32])=[CH:26][C:25]=3[O:55][CH3:56])[N:14]=2)=[CH:4][CH:3]=1.BrC1N=C(C(=O)NC)C(NC2C(C(F)(F)F)=CN=C(NC3C=CC(CP(=O)(O)OCC)=CC=3OC)N=2)=CC=1.CC1(C)C(C)(C)OB(C2C=NN(CC[C@@H](O)C)C=2)O1>>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:54]=[CH:53][C:27]([CH2:28][P:29](=[O:52])([O:33][C@H:34]([CH2:36][CH2:37][N:38]4[CH:42]=[C:41]([B:43]5[O:47][C:46]([CH3:49])([CH3:48])[C:45]([CH3:50])([CH3:51])[O:44]5)[CH:40]=[N:39]4)[CH3:35])[O:30][CH2:31][CH3:32])=[CH:26][C:25]=3[O:55][CH3:56])[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 67812823(2S)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-ol2×HCID 86697762Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate2×HCID 86697847ethyl (2R)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 86697848Ethyl (2S)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Procedure

Racemic Compound 70A was prepared analogously to Compound 69A using ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 38C, 1 g, 2 mmol) and (25)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-ol (Compound 70B, 400 mg, 2 mmol) to afford 454 mg of the title compound as a mixture of diastereomers (30%). MS (ESI): m/z=867.82/869.81 [M+H]+. UPLC: tR=1.69 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-6d8e5876bc4341c897bbd71de826c395
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…