p-(Trifluoromethoxy)phenyl isocyanate → HCID 58451290, compound

HRID 2366788Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[F:24])[O:5][C:6]1[N:11]=[C:10]2[S:12][C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])=[N:14][C:9]2=[CH:8][CH:7]=1.[N:25]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1)=[C:26]=[O:27]>N1C=CC=CC=1.C(OCC)(=O)C.O1CCCC1.CCCCCC>[F:24][C:23]1[CH:22]=[CH:21][C:4]([O:5][C:6]2[N:11]=[C:10]3[S:12][C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])=[N:14][C:9]3=[CH:8][CH:7]=2)=[CH:3][C:2]=1[NH:1][C:26](=[O:27])[NH:25][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:36])([F:38])[F:37])=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-[5-(3-Amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.44 mmol) was dissolved in pyridine (3.0 mL), 1-isocyanato-4-(trifluoromethoxy)benzene (99 μL, 0.66 mmol) was added, and the mixture was stirred at 70° C. for 2 hr. 1-Isocyanato-4-(trifluoromethoxy)benzene (20 μL, 0.13 mmol) was added to the reaction mixture, and the mixture was further stirred at 70° C. for 3 hr. The obtained suspension was cooled to room temperature, and diluted with ethyl acetate (5 mL), tetrahydrofuran (1 mL) and n-hexane (5 mL). The precipitated resultant product was collected by filtration to give the title compound (177 mg, 74%) as a colorless powder.

Workup

stirringthe mixture was further stirred at 70° C. for 3 hr
temperatureThe obtained suspension was cooled to room temperature
customThe precipitated resultant product
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-cd45abc82cdb4097937e6b48aaa5633d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697874B2

Reaction notes

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