Sodium borohydride → HCID 57584942, compound

HRID 2077569Notes

Reaction equation

HRID 2077569 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]([C:21]3[CH:33]=[CH:32][C:24]4[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=4[CH:22]=3)[CH:17]=[N:18][C:19]=2[Cl:20])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO.O.CS(C)=O>[Cl:20][C:19]1[N:18]=[CH:17][C:16]([C:21]2[CH:33]=[CH:32][C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=2)=[CH:15][C:14]=1[NH:13][S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][CH:8]=1)(=[O:12])=[O:11]

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 57585085HCID 57585085, compound

Product 1

HCID 57584942HCID 57584942, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(6-(5-(4-acetylphenylsulfonamido)-6-chloropyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.050 g, 0.10 mmol) in THF (5 mL) and MeOH (5 mL) was added sodium borohydride (0.009 mL, 0.3 mmol) at RT. The resultant was stirred at RT for 1 h, and then diluted with 3 mL of water and 1 mL of DMSO. The resultant was filtered. The filterate was subjected to reverse phase HPLC (5-60% CH3CN in water) purification to give a white solid (30 mg, 60%). MS (ESI pos. ion) Found m/z: 541, (M+K)+.

Workup

  1. filtrationThe resultant was filtered
  2. customphase HPLC (5-60% CH3CN in water) purification

Sources & evidence

ORD record
ord-bba7018692814f63b35bbdfb68fc0b4c
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…