4-Pyridinecarboxaldehyde → HCID 10454518, compound

HRID 227502Notes

Reaction equation

HRID 227502 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([NH2:13])=[O:12])=[C:7]2[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].[CH:23]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)=O.[BH4-].[Na+]>CO>[N:17]1([S:14]([C:7]2[C:6]3[C:10](=[C:2]([NH:1][CH2:23][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[CH:3]=[CH:4][CH:5]=3)[NH:9][C:8]=2[C:11]([NH2:13])=[O:12])(=[O:16])=[O:15])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 100191367-Amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide

Product 1

HCID 10454518HCID 10454518, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide from Example 7 (36 mg, 0.11 mmol) in 1 mL of methanol was added 4-formylpyridine (24 mg, 0.22 mmol). After stirring overnight, sodium borohydride was added (13 mg, 0.33 mmol). After 2 hours, the reaction was quenched with 3N HCl, concentrated in vacuo, taken up in DMF, and purified by preparative reversed phase HPLC. The titled product was obtained as a yellow solid. Proton NMR for the product was consistent with the titled compound. ESI+MS: 416.4 [M+H]+.

Workup

  1. waitAfter 2 hours
  2. customthe reaction was quenched with 3N HCl
  3. concentrationconcentrated in vacuo
  4. custompurified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-b2ed350bc6ca458c9a4e8bb066558194
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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