Water → HCID 86674812, compound

HRID 1520784Notes

Reaction equation

HRID 1520784 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)=[CH:11][CH:10]=2)=[O:7])=[N:2]1.Cl[C:29]1[N:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:36][C:35]([F:38])([F:37])[C:32]1[CH:31]=[N:30][C:29]([N:1]2[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([C@@H:15]4[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]4)=[CH:11][CH:10]=3)=[O:7])=[N:2]2)=[N:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 133170192-Chloro-5-(trifluoromethyl)pyrimidineHCID 178452471HCID 178452471, compound

Product 1

HCID 86674812HCID 86674812, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(S)-tert-Butyl 2-(4-(1H-pyrazole-3-carboxamido)phenyl)morpholine-4-carboxylate (33 mg, 0.089 mmol) and 2-chloro-5-(trifluoromethyl)pyrimidine (16.2 mg, 0.089 mmol) were dissolved in DMSO (0.7 ml) and potassium carbonate (24.5 mg, 0.177 mmol) was added. The reaction mixture was placed on a Büchi shaker for 20 hours at 120° C. After cooling the mixture, water was added followed by extraction with ethyl acetate twice. The combined organic layers were dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (silica gel, 5 g, 25% to 50% EtOAc in heptane) to yield an off-white solid (11 mg, 24%). MS (ISP): 463.1 (100%, [M−tBu+H]+), 519.3 (10%, [M+H]+).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate twice
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customevaporated
  5. customThe crude material was purified by flash chromatography (silica gel, 5 g, 25% to 50% EtOAc in heptane)

Sources & evidence

ORD record
ord-39d214e8b1be43d699695e74340e0e74
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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