Dimethylformamide → HCID 178478952, compound

HRID 893702Notes

Reaction equation

HRID 893702 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]3[N:22]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:21]4[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=4[N:19]=3)[CH2:13][CH2:12]2)[C:3]=1[NH2:35].[C:36](=[S:38])=[S:37].CN(C)C=O>O>[ClH:1].[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:22]2[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=[C:18]2[NH:17][CH:14]2[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:4]3[C:3]4[N:35]=[C:36]([SH:38])[S:37][C:2]=4[N:7]=[CH:6][N:5]=3)[CH2:12][CH2:13]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6348Carbon DisulfideHCID 13588146HCID 13588146, compound

Product 1

HCID 178478952HCID 178478952, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7 parts of 6-chloro-N4 -[2-[4-[[-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4,5-pyrimidinediamine, 2.1 parts of carbon disulfide and 90 parts of N,N-dimethylformamide was stirred overnight at 70° c. The reaction mixture was poured into water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from ethanol. The product was filtered off and dried in vacuo overnight at 120° C., yielding 2.3 parts (29%) of 7-[[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]amino]-thiazolo[5,4-d]pyrimidine-2-thiol monohydrochloride; mp. 226.5° C. (compound 148).

Workup

  1. extractionThe product was extracted with trichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized from ethanol
  6. filtrationThe product was filtered off
  7. customdried in vacuo overnight at 120° C.

Sources & evidence

ORD record
ord-d11ea46af58a4931b1a13f7d1395e046
Source dataset
uspto-grants-1992_06
Patent number
US05126339

Reaction notes

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