Diisopropylethylamine → HCID 118223431, compound

HRID 2200206Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][CH:3]=1.[O:21]([C:28]([NH:30][C:31]1[CH:32]=[C:33]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1)[O:34][CH2:35][CH:36]1[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:37]1)=O)C1C=CC=CC=1.CCN(C(C)C)C(C)C>C1COCC1>[CH:16]1([C:14]([NH:13][C:9]2[CH:8]=[C:7]([O:6][C:5]3[CH:19]=[CH:20][C:2]([NH:1][C:28]([NH:30][C:31]4[CH:32]=[C:33]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=4)[O:34][CH2:35][CH:36]4[CH2:37][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39]4)=[O:21])=[CH:3][CH:4]=3)[CH:12]=[CH:11][N:10]=2)=[O:15])[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 70 °C

Procedure

Dissolve N-[4-(4-aminophenoxy)-2-pyridyl]cyclopropanecarboxamide (200 mg, 0.74 mmol) and tert-butyl 3-[[3-(phenoxycarbonylamino)-5-(trifluoromethyl)phenoxy]methyl]-azetidine-1-carboxylate (415 mg, 0.89 mmol) in THF (10 mL), add DIEA (200 mg, 1.48 mmol), stir under N2 at 70° C. for 12 hrs. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=2:1) affords the title compound (250 mg, 52.4%). MS: (M+1): 642.3.

Workup

concentrationConcentrate under reduced pressure
customto give the crude product
customPurification by chromatography (silica gel, EtOAc:PE=2:1)

Sources & evidence

ORD record: ord-2292a605eeac4467b47b2b4623c71ee3
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359338B2

Reaction notes

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