Sodium cyanoborohydride → HCID 90260014, compound

HRID 1478137Notes

Reaction equation

HRID 1478137 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[NH:8][C:5]2=[N:6][CH:7]=1.[CH:14]([C:16]1[CH:17]=[C:18]([CH:28]=[CH:29][CH:30]=1)[C:19]([NH:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:20])=O.[BH3-]C#N.[Na+]>CO.CC(O)=O>[C:11]([C:9]1[NH:8][C:5]2=[N:6][CH:7]=[C:2]([NH:1][CH2:14][C:16]3[CH:17]=[C:18]([CH:28]=[CH:29][CH:30]=3)[C:19]([NH:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[O:20])[CH:3]=[C:4]2[CH:10]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 67155917HCID 67155917, compoundHCID 90258783HCID 90258783, compound

Product 1

HCID 90260014HCID 90260014, compound

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

1-(5-Amino-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanone (1 eq) and 3-Formyl-N-pyridin-3-yl-benzamide (1.1 eq) were stirred in a mixture of MeOH/AcOH (10/1; 0.06M) for 2 h. Then NaBH3CN (1.2 eq) was slowly added and the mixture was stirred under argon at RT overnight. The reaction was quenched by addition of saturated NaHCO3 solution until neutrality. MeOH and acetic acid were evaporated. The crude was filtered and washed with water and Et2O before being purified on reverse phase (H2O 1% TFA/MeCN 1% TFA 100/0, 0/100). MeCN was evaporated. The product was suspended in H2O and basified with saturated NaHCO3 solution until pH=8-9. The aqueous layer was extracted three times with AcOEt. The organic layer was dried over Na2SO4, filtered and concentrated to give the expected product.

Workup

  1. customThe reaction was quenched by addition of saturated NaHCO3 solution until neutrality
  2. customMeOH and acetic acid were evaporated
  3. filtrationThe crude was filtered
  4. washwashed with water and Et2O
  5. custombefore being purified on reverse phase (H2O 1% TFA/MeCN 1% TFA 100/0, 0/100)
  6. customMeCN was evaporated
  7. extractionThe aqueous layer was extracted three times with AcOEt
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ff39d62637dd4ec1a04e8ae9c6d6b11b
Source dataset
uspto-grants-2016_08
Patent number
US09403823B2

Reaction notes

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