1-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → Diethyl (4-{[4-({2-(methylcarbamoyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 511332Notes

Reaction equation

HRID 511332 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]([NH:19][C:20]3[CH:34]=[CH:33][C:23]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:22][CH:21]=3)[N:10]=2)=[C:4]([C:35](=[O:38])[NH:36][CH3:37])[CH:3]=1.[CH2:39]([N:43]1[CH:47]=[C:46](B2OC(C)(C)C(C)(C)O2)[CH:45]=[N:44]1)[CH:40]([CH3:42])[CH3:41]>>[CH3:37][NH:36][C:35]([C:4]1[CH:3]=[C:2]([C:46]2[CH:45]=[N:44][N:43]([CH2:39][CH:40]([CH3:42])[CH3:41])[CH:47]=2)[CH:7]=[CH:6][C:5]=1[NH:8][C:9]1[C:14]([C:15]([F:16])([F:18])[F:17])=[CH:13][N:12]=[C:11]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([CH2:24][P:25](=[O:32])([O:26][CH2:27][CH3:28])[O:29][CH2:30][CH3:31])=[CH:33][CH:34]=2)[N:10]=1)=[O:38]

Participants

3

Reactant 2

HCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 49821189Diethyl (4-{[4-{[4-bromo-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Product 1

HCID 58293065Diethyl (4-{[4-({2-(methylcarbamoyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Procedure

The title compound was prepared using the procedure from Example 97 with Diethyl (4-{[4-{[4-bromo-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (Example 106) and the commercially available 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. MS (ES+): m/z 666.20(100) [MH+]; HPLC: tR=3.60 min (ZQ3, polar—5 min).

Workup

  1. custom5 min

Sources & evidence

ORD record
ord-255a458c24fd4606991e5854ba4f9e60
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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