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

HRID 2068764Notes

Reaction equation

HRID 2068764 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 vacum 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 vacum at 70° C. the title compound

Sources & evidence

ORD record
ord-cb10ba36b95345f2bb6579457d600c74
Source dataset
uspto-grants-2012_10
Patent number
US08299057B2

Reaction notes

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