Water → HCID 178420199, compound

HRID 1792592Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:10]2[CH:11]=[C:12]([C:15]3[C:16]([C:39]4[S:43][C:42]([C:44]#[N:45])=[CH:41][CH:40]=4)=[N:17][N:18]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1.[N-:46]=[N+:47]=[N-:48].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[NH:46]1[C:44]([C:42]2[S:43][C:39]([C:16]3[C:15]([C:12]4[CH:13]=[CH:14][C:9]5[N:10]([C:6]([C:2]6[S:1][CH:5]=[CH:4][N:3]=6)=[CH:7][N:8]=5)[CH:11]=4)=[CH:19][N:18]([C:20]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:17]=3)=[CH:40][CH:41]=2)=[N:45][N:48]=[N:47]1

Participants

Conditions

Temperature: 100 °C

Procedure

100 mg 5-[4-(3-thiazol-2-yl-imidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]-thiophen-2-carbonitrile (compound in Example 440) was dissolved in 3 mL N,N-dimethylformamide, and 12 mg sodium azide and 9.5 mg ammonium chloride were added thereto and stirred at 100° C. for 18 hours in a stream of nitrogen. 24 mg sodium azide and 19 mg ammonium chloride were further added thereto and stirred for additional 24 hours. Water was added to the reaction solution which was then extracted with ethyl acetate and purified by silica gel column chromatography (ethyl acetate/hexane), to give 60 mg of the title compound (pale pink solid).

Workup

stirringstirred for additional 24 hours
extractionwas then extracted with ethyl acetate
custompurified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-3fc754ced135477ab9603d9cc21b95dc
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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