Imidazole → HCID 118272464, compound

HRID 590784Notes

Reaction equation

HRID 590784 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.N1C=CN=C1.[Cl:18][C:19]1[N:24]=[CH:23][C:22]2[C:25]([NH2:47])=[N:26][N:27]([C:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:21]=2[CH:20]=1.Cl.[F:49][C:50]1([F:54])[CH2:53][NH:52][CH2:51]1>C(Cl)Cl>[Cl:18][C:19]1[N:24]=[CH:23][C:22]2[C:25]([NH:47][C:6]([N:52]3[CH2:53][C:50]([F:54])([F:49])[CH2:51]3)=[O:7])=[N:26][N:27]([C:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 118272274HCID 118272274, compound

Product 1

HCID 118272464HCID 118272464, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di(1H-imidazol-1-yl)methanone (197 mg, 1.217 mmol) was added to a stirred mixture of 1H-imidazole (166 mg, 2.434 mmol) and 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (250 mg, 0.608 mmol) in CH2Cl2 (4 ml) and the mixture was stirred at room temperature for overnight. The second day, 3,3-difluoroazetidine hydrochloride (190 mg) was added and the mixture was heated at 50° C. for 3 hours, LCMS and TLC showed clean reaction. The mixture was directly loaded to a silica gel column eluting with EtOAc/Hexane=0% to 100% gradient to give N-(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)-3,3-difluoroazetidine-1-carboxamide (320 mg, 0.604 mmol, 99% yield).

Workup

  1. temperaturethe mixture was heated at 50° C. for 3 hours
  2. customreaction
  3. washeluting with EtOAc/Hexane=0% to 100% gradient

Sources & evidence

ORD record
ord-f5436c1e0ca04bd5b1a715f3abfbe016
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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