Water → HCID 86671414, compound

HRID 2403338Notes

Reaction equation

HRID 2403338 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.Cl[C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[N:25]=[CH:24][N:23]=1.C(N(C(C)C)CC)(C)C.O>CC(N(C)C)=O>[F:29][C:28]([F:31])([F:30])[C:26]1[N:25]=[CH:24][N:23]=[C:22]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C@H:8]3[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)=[CH:4][CH:3]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 115428814-Chloro-6-(trifluoromethyl)pyrimidineHCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

Product 1

HCID 86671414HCID 86671414, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (5)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (100 mg, 0.36 mmol), 4-chloro-6-(trifluoromethyl)pyrimidine (72 mg, 0.4 mmol) and diisopropylethylamine (70 mg, 0.54 mmol) was dissolved in dimethylacetamide (1.3 ml) and stirred at 80° C. overnight. For work-up water was added, and the mixture was extracted with ethyl acetate twice. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (10 g silica gel, 20 to 40% ethyl acetate in heptane) to yield a white solid (135 mg, 89%). MS (ISP): 425.2 ([M+H]+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (10 g silica gel, 20 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-fe5412c0e2cc4afb8e47d54dfbd74fd2
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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