Sodium cyanoborohydride → HCID 54173271, compound

HRID 260546Notes

Reaction equation

HRID 260546 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1C=CC(S(OCC)(=O)=O)=CC=1.[CH3:21][N:22]([CH:24]=[N:25][S:26]([C:29]1[C:30]([C:35]2[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37][CH:36]=2)=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27])[CH3:23].C([BH3-])#N.[Na+]>ClCCl>[C:6]([CH:2]([NH:1][CH2:41][C:38]1[CH:39]=[CH:40][C:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[S:26]([N:25]=[CH:24][N:22]([CH3:23])[CH3:21])(=[O:28])=[O:27])=[CH:36][CH:37]=1)[C:3]([O:5][CH2:8][CH3:9])=[O:4])#[N:7]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 54273713N'-(4'-Formyl[1,1'-biphenyl]-2-sulfonyl)-N,N-dimethylmethanimidamideHCID 86749579HCID 86749579, compound

Product 1

HCID 54173271HCID 54173271, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g of ethyl mono (4-methylbenzenesulfonate) aminocyano acetate of Stage B of Example 1 and 1.9 g of N-[(dimethylamino) methylene]-4'-formyl-(1,1'-biphenyl)-2-sulfonamide of Stage A of Example 1 were stirred in dichloromethane at 35° for 3 hours and then 0.396 g of sodium cyano borohydride were added. The solution was stirred at ambient temperature for 18 hours and the reaction mixture was filtered, washed with water and evaporated. After chromatography on silica (dichloromethane-ethyl acetate 85-15), 770 mg of the expected product were obtained, identical to that of Stage C of Example 1.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with water
  3. customevaporated

Sources & evidence

ORD record
ord-103d0109561a4abead21deeda985d7ac
Source dataset
uspto-grants-1996_06
Patent number
US05527919

Reaction notes

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