Dichloromethane → 2-Amino-5,7-dimethyl-3-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-3h-imidazo[4,5-b]pyridine di-hydrochloride

HRID 858517Notes

Reaction equation

HRID 858517 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19][C:20]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[O:21])=[CH:13][CH:12]=2)=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8].Br[C:34]#[N:35].C(Cl)[Cl:37]>C1COCC1.O>[ClH:37].[ClH:37].[NH2:35][C:34]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19][C:20]([NH:22][S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)(=[O:25])=[O:24])=[O:21])=[CH:13][CH:12]=2)[C:3]2=[N:4][C:5]([CH3:9])=[CH:6][C:7]([CH3:8])=[C:2]2[N:1]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 218756203-Amino-4,6-dimethyl-2-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}anilino)pyridine

Product 1

HCID 218758592-Amino-5,7-dimethyl-3-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-3h-imidazo[4,5-b]pyridine di-hydrochlorideYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-{[(2-{4-[(3-amino-4,6-dimethyl-2-pyridinyl)amino]phenyl}ethyl)amino]carbonyl}-4-methylbenzenesulfonamide (300 mg, 0.66 mmol) in THF (6 ml) was added a solution of BrCN (175 mg, 1.65 mmol) in water (2 ml). The resultant mixture was stirred at room temperature for 16 hours. The mixture was diluted with CH2Cl2 and washed with brine. The organic layer was dried over MgSO4 and filtered. After concentration in vacuo, the residue was purified by preparative TLC (CH2Cl2/MeOH=10/1) to afford 224 mg (71%) of the title compound.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationAfter concentration in vacuo
  5. customthe residue was purified by preparative TLC (CH2Cl2/MeOH=10/1)

Sources & evidence

ORD record
ord-908e06c550764f07abf450af6e9ffcc6
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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