1,2-Dichloroethane → racemic 2-hydroxy-2-methyl-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanamide

HRID 595283Notes

Reaction equation

HRID 595283 reaction equation
[OH:1][C:2]([CH3:30])([CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[C:16]([NH:18][C:19]3[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][N:20]=3)[CH:15]=[C:14]([CH3:29])[CH:13]=2)[CH:9]=[N:8]1)[C:3]([OH:5])=O.C1C=CC2N(O)N=[N:37]C=2C=1.C(Cl)CCl.[Cl-].[NH4+].C(N(CC)CC)C>CCOC(C)=O.O.[Cl-].[Na+].O.CN(C=O)C>[OH:1][C:2]([CH3:30])([CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[C:16]([NH:18][C:19]3[N:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][N:20]=3)[CH:15]=[C:14]([CH3:29])[CH:13]=2)[CH:9]=[N:8]1)[C:3]([NH2:37])=[O:5]

Participants

10

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 118208615racemic 2-hydroxy-2-methyl-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanoic acid

Product 1

HCID 118208526racemic 2-hydroxy-2-methyl-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanamide

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Racemic 2-hydroxy-2-methyl-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanoic acid (142 mg, 0.26 mmol), HOBT (61 mg, 0.4 mmol), EDC (76 mg, 0.4 mmol), and ammonium chloride (42.5 mg, 0.8 mmol) were combined with DMF (2.5 mL) in a flask. Triethylamine (0.35 mL, 2.51 mmol) was added and the mixture was stirred for 3 days at room temperature. The mixture was diluted with EtOAc and diluted with 1:1 water:brine (3×). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford racemic 2-hydroxy-2-methyl-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanamide. MS ESI calcd. for C19H19F3N6O2 [M+H]+ 421. found 421.

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dec8a0516b4a4df082ff10598d1657af
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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