Diisopropylethylamine → HCID 118223423, compound

HRID 2200202Notes

Reaction equation

HRID 2200202 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=O)[O:22]C4C=CC=CC=4)=[C:16]([CH3:30])[CH:15]=3)[CH:8]=2)=[O:5])[CH2:3][CH2:2]1.[CH:31]([NH:34][C:35]1[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([NH2:45])[CH:36]=1)([CH3:33])[CH3:32].CCN(C(C)C)C(C)C>C1COCC1>[CH:31]([NH:34][C:35]1[CH:36]=[C:37]([NH:45][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][C:9]3[N:10]=[CH:11][N:12]=[C:7]([NH:6][C:4]([CH:1]4[CH2:2][CH2:3]4)=[O:5])[CH:8]=3)=[CH:15][C:16]=2[CH3:30])=[O:22])[CH:38]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:40]=1)([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90020062HCID 90020062, compoundHCID 118223415HCID 118223415, compound

Product 1

HCID 118223423HCID 118223423, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve phenyl N-[4-[6-(cyclopropanecarbonylamino)pyrimidin-4-yl]oxy-2-methyl-phenyl]carbamate (343 mg, 1.57 mmol), N1-isopropyl-5-(trifluoromethyl)benzene-1,3-diamine (700 mg, 1.73 mmol) and DIEA (608 mg, 4.72 mmol) in THF (4 mL), heat the reaction at 80° C. for 3 hrs. After the reaction is complete, remove the volatiles under reduced pressure. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (450 mg, 83%). MS: (M+1): 529.3.

Workup

  1. temperatureheat
  2. customthe reaction at 80° C. for 3 hrs
  3. customremove the volatiles under reduced pressure
  4. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-e6055e02e9454e8e91be5edcbae7b534
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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