Trifluoroacetic acid → HCID 178485254, compound

HRID 2279899Notes

Reaction equation

HRID 2279899 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15](Cl)[N:14]=2)=[C:6]([CH:11]=1)[C:7]([NH:9][CH3:10])=[O:8].[NH2:24][C:25]1[CH:54]=[CH:53][C:28]([CH2:29][CH2:30][CH2:31][CH2:32][PH:33](=[O:52])[O:34][CH2:35][CH2:36][CH2:37][N:38]2[CH:42]=[C:41]([B:43]3[O:47][C:46]([CH3:49])([CH3:48])[C:45]([CH3:51])([CH3:50])[O:44]3)[CH:40]=[N:39]2)=[CH:27][C:26]=1[O:55][CH3:56].C(O)(C(F)(F)F)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:24][C:25]3[CH:54]=[CH:53][C:28]([CH2:29][CH2:30][CH2:31][CH2:32][PH:33](=[O:52])[O:34][CH2:35][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)=[CH:27][C:26]=3[O:55][CH3:56])[N:14]=2)=[C:6]([C:7](=[O:8])[NH:9][CH3:10])[CH:11]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86697835HCID 86697835, compound2×HCID 178490211HCID 178490211, compound2×

Product 1

HCID 178485254HCID 178485254, compound

Conditions

Temperature
50 °C

Procedure

A solution of 5-bromo-2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (Compound 66B, 150.5 mg, 0.3674 mmol) and 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propyl (4-amino-3-methoxybenzyl)propylphosphinate (Compound 66C, 175.4 mg, 0.3674 mmol) in TFE (5.0 mL) was charged with TFA (0.0602 mL). The reaction mixture was stirred at 50° C. for 24 hours. The reaction mixture was concentrated under reduced pressure to a light yellow oil and purified on a Teledyne ISCO Combiflash® Rf system using DCM/MeOH (100:0→90:10) as eluent to afford the racemic title compound as 0.245 g of a white solid (78%). MS (ESI): m/z 850.91/852.88 [M+H]+. UPLC: tR=1.52 min (UPLC-SQD: analytical—2 min).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a light yellow oil
  2. custompurified on a Teledyne ISCO Combiflash® Rf system

Sources & evidence

ORD record
ord-a35a7d1d5ac5459e880efcb071d632e3
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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