Cyanogen Bromide → HCID 178480620, compound

HRID 1163436Notes

Reaction equation

HRID 1163436 reaction equation
[NH2:1][C:2]1[C:19]([NH2:20])=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([N:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[CH:3]=1.[N:28]#[C:29]Br>CCO.C(OCC)C>[NH:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([NH:8][C:6]([C:5]3[C:4]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:3][C:2]4[NH:1][C:29]([NH2:28])=[N:20][C:19]=4[CH:18]=3)=[O:7])[CH:17]=2)[CH:13]=[N:14]1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 68443410HCID 68443410, compound

Product 1

HCID 178480620HCID 178480620, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4,5-diamino-2-(4-methylpiperazin-1-yl)-N-(1H-indazol-6-yl)-benzamide (2 mmol; see Example 181) in 10% aqueous EtOH (6 mL) was added cyanogen bromide (2.2 mmol), and the mixture was heated at reflux for 4 h. The reaction mixture was then concentrated in vacuo, and the residue obtained was suspended in diethyl ether with vigorous stirring. The solid obtained was collected by filtration, washed with diethyl ether, and dried in vacuo to afford 2-amino-6-(4-methylpiperazin-1-yl)-1H-benzimidazole-5-carboxylic acid (1H-indazol-6-yl)-amide as a hydrobromide salt. MS: m/z 391 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customthe residue obtained
  5. customThe solid obtained
  6. filtrationwas collected by filtration
  7. washwashed with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-58b6101319094fdbb9ae75bbb6093257
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

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