Diisopropylethylamine → HCID 118223399, compound

HRID 2200203Notes

Reaction equation

HRID 2200203 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])OC4C=CC=CC=4)=[CH:16][C:15]=3[F:30])[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1.[NH2:31][C:32]1[CH:33]=[C:34]([CH:42]([N:44]2[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]2)[CH3:43])[CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:31][C:32]4[CH:33]=[C:34]([CH:42]([N:44]5[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:54])([CH3:56])[CH3:55])=[O:51])[CH2:46][CH2:45]5)[CH3:43])[CH:35]=[C:36]([C:38]([F:40])([F:41])[F:39])[CH:37]=4)=[O:29])=[CH:16][C:15]=3[F:30])[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90027336HCID 90027336, compoundHCID 90034030HCID 90034030, compound

Product 1

HCID 118223399HCID 118223399, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add phenyl N-[4-[[2-(cyclopropanecarbonylamino)-4-pyridyl]oxy]-3-fluoro-phenyl]carbamate (220 mg, 0.53 mmol), tert-butyl 4-[1-[3-amino-5-(trifluoromethyl)phenyl]-ethyl]piperazine-1carboxylate (165 mg, 0.442 mmol) and DIEA (120 mg, 0.88 mmol) in THF (10 mL), stir the reaction under N2 at 80° C. for 12 hrs. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (230 mg, 75.6%).

Workup

  1. customthe reaction under N2 at 80° C. for 12 hrs
  2. concentrationConcentrate under reduced pressure
  3. customto give the crude product
  4. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-65c87e5c1a764be384f8782854d8ee8c
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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