Tetrahydrofuran 2-propanol → (3-amino-1-trityl-1H-indazol-5-yl)(3,5-difluorophenyl)methanone

HRID 1526004Notes

Reaction equation

HRID 1526004 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[C:43]([F:45])[CH:44]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:11]=[C:10]2[NH:35]C(=O)C(F)(F)F)=[O:6].C(O)(C)C.O1CCCC1>C(N(CC)CC)C>[NH2:35][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:5]([C:4]3[CH:42]=[C:43]([F:45])[CH:44]=[C:2]([F:1])[CH:3]=3)=[O:6])[CH:8]=2)[N:12]([C:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=1

Participants

4

Reactant 2

HCID 22597222Tetrahydrofuran 2-propanolHCID 86647614N-(5-(3,5-Difluorobenzoyl)-1-trityl-1H-indazol-3-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 68670918(3-amino-1-trityl-1H-indazol-5-yl)(3,5-difluorophenyl)methanoneYield 99%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-[5-(3,5-Difluoro-benzoyl)-1-trityl-1H-indazol-3-yl]-2,2,2-trifluoro-acetamide (6.12 g, 10 mmol) was heated at 100° C. in a mixture isopropanol/tetrahydrofuran 8:2 (100 mL) and triethylamine (12.2 mL) for 48 hours. The volatiles were partially evaporated and the resulting mixture cooled and filtered. The solid was washed with diethyl ether. After drying under vacuum at 70° C. the title compound was obtained as a white solid (5.1 g, 99% yield).

Workup

  1. customThe volatiles were partially evaporated
  2. temperaturethe resulting mixture cooled
  3. filtrationfiltered
  4. washThe solid was washed with diethyl ether
  5. dry with materialAfter drying under vacuum at 70° C. the title compound

Sources & evidence

ORD record
ord-d445fdb395d04ecda8c1abc34b9c97af
Source dataset
uspto-grants-2015_07
Patent number
US09085558B2

Reaction notes

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