Sodium cyanoborohydride → HCID 56967032, compound

HRID 1468185Notes

Reaction equation

HRID 1468185 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][N:12]([CH2:14][C:15]3[CH:16]=[C:17]([CH:35]=[CH:36][CH:37]=3)[C:18]([NH:20][C:21]3[S:22][C:23]4[CH2:29][C@H:28]([NH:30][CH2:31][CH2:32][O:33][CH3:34])[CH2:27][CH2:26][C:24]=4[N:25]=3)=[O:19])[CH:13]=2)=[CH:5][CH:4]=1)#[N:2].[C:38]([BH3-])#N.[Na+]>CO.C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[N:11][N:12]([CH2:14][C:15]3[CH:16]=[C:17]([CH:35]=[CH:36][CH:37]=3)[C:18]([NH:20][C:21]3[S:22][C:23]4[CH2:29][C@H:28]([N:30]([CH2:31][CH2:32][O:33][CH3:34])[CH3:38])[CH2:27][CH2:26][C:24]=4[N:25]=3)=[O:19])[CH:13]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 56967031HCID 56967031, compound

Product 1

HCID 56967032HCID 56967032, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21906813HCID 21906813, compoundSolvent

Procedure

Add to a solution of 3-[4-(4-cyano-phenyl)-[1,2,3]triazol-1-ylmethyl]-N—[(R)-6-(2-methoxy-ethylamino)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-benzamide (0.13 g, 0.20 mmol) in 5 mL MeOH formalin (0.3 mL) and sodium cyanoborohydride (51 mg, 0.82 mmol). Stir the mixture at room temperature for 2 h. Add sat. NH4Cl to the mixture to quench any unreacted sodium cyanoborohydride. Concentrate the mixture, concentrate and purify via preparative HPLC to afford 0.06 g, 58% yield of 3-[4-(4-cyano-phenyl)-[1,2,3]triazol-1-ylmethyl]-N-{(R)-6-[(2-methoxy-ethyl)-methyl-amino]-4,5,6,7-tetrahydro-benzothiazol-2-yl}-benzamide. MS, ES+ 528.44 (M+H), rt 5.33 min

Workup

  1. customAdd sat. NH4Cl to the mixture to quench any unreacted sodium cyanoborohydride
  2. concentrationConcentrate the mixture
  3. concentrationconcentrate
  4. custompurify via preparative HPLC

Sources & evidence

ORD record
ord-1987597162ef4e368bd27f71bc570065
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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