Diethyl (4-{[4-{[4-bromo-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate → Diethyl (4-{[4-({4-[1-(3-hydroxycyclobutyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 1947902Notes

Reaction equation

HRID 1947902 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.C([Si](C)(C)[O:44][CH:45]1[CH2:48][CH:47]([N:49]2[CH:53]=[C:52](B3OC(C)(C)C(C)(C)O3)[CH:51]=[N:50]2)[CH2:46]1)(C)(C)C>>[OH:44][CH:45]1[CH2:48][CH:47]([N:49]2[CH:53]=[C:52]([C:2]3[CH:7]=[CH:6][C:5]([NH:8][C:9]4[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]([NH:19][C:20]5[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]=5)[N:10]=4)=[C:4]([C:35](=[O:38])[NH:36][CH3:37])[CH:3]=3)[CH:51]=[N:50]2)[CH2:46]1

Participants

3

Reactant 2

HCID 49821189Diethyl (4-{[4-{[4-bromo-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonateHCID 672540531-(3-{[tert-butyl(dimethyl)silyl]oxy}cyclobutyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 58292984Diethyl (4-{[4-({4-[1-(3-hydroxycyclobutyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)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 1-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (Compound 100A). After Suzuki reaction and SPE pre-purification, dried material was dissolved in DCM and 1.0 M HCl in ether was added. The mixture was stirred at room temperature for half an hour. The crude was sent to MDP for purification. MS (ES+): m/z 674.34 (100) [MH+]; HPLC: tR=0.94 min (UPLC, purity).

Workup

  1. customAfter Suzuki reaction
  2. custompre-purification, dried material
  3. dissolutionwas dissolved in DCM
  4. addition1.0 M HCl in ether was added
  5. customThe crude was sent to MDP for purification

Sources & evidence

ORD record
ord-f3a85951a0254755bff4b2ffbd34434b
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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