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Water → HCID 90416605, compound

HRID 576174
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Reaction equation

HRID 576174 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15])[CH3:2].[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[C:24]([F:32])[CH:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>C(Cl)Cl>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]([CH3:19])([CH3:18])[C:4]([O:3][CH2:1][CH3:2])=[O:20])=[C:8]([C:14]([F:15])([F:17])[F:16])[CH:9]=2)=[O:30])=[C:24]([F:32])[CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 140537922-(4-Bromo-2-fluorophenyl)acetic acidHCID 90416545HCID 90416545, compound

Product 1

HCID 90416605HCID 90416605, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl-3-(4-amino-2-(trifluoromethyl)phenyl)-2,2-dimethylpropanoate (200 mg, 0.691 mmol) was added to a solution of 2-(4-bromo-2-fluorophenyl)acetic acid (161 mg, 0.691 mmol), HATU (315 mg, 0.830 mmol) and TEA (0.482 mL, 3.46 mmol) in DCM (5 mL). The reaction mixture was stirred at rt for 2 h, and then the solution was distributed between DCM and H2O. The combined organic extract was dried over MgSO4, filtered and concentrated. The crude product was purified by preparative TLC (DCM, Rf=0.5) to yield a light yellow oil of ethyl 3-(4-(2-(4-bromo-2-fluorophenyl)acetamido)-2-(trifluoromethyl)phenyl)-2,2-dimethylpropanoate (320 mg, 0.571 mmol, 83.0% yield): 1H NMR (400 MHz, MeOH-d4) δ 7.94 (d, J=1.54 Hz, 1H), 7.68 (d, J=8.38 Hz, 1H), 7.27-7.36 (m, 2H), 7.22 (d, J=8.38 Hz, 1H), 6.90-6.97 (m, 1H), 4.09-4.18 (m, 2H), 3.74 (s, 2H), 3.07 (s, 2H), 1.20-1.25 (m, 3H), 1.15 (s, 6H); ES-LCMS m/z 504 (M+H).

Workup

  1. extractionThe combined organic extract
  2. dry with materialwas dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative TLC (DCM, Rf=0.5)

Sources & evidence

ORD record
ord-046001c8c31f40bb8734e13a666b7060
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09035063B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes