Hydrochloric Acid → N-(5-cyanopyridin-2-yl)-2-formyl-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxamide

HRID 1778106Notes

Reaction equation

HRID 1778106 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]3[CH:20]=[CH:21][C:22]([CH:24](OC)[O:25]C)=[N:23][C:14]2=3)=[O:12])=[N:8][CH:9]=1)#[N:3].C([O-])(O)=O.[Na+]>C1COCC1>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]3[CH:20]=[CH:21][C:22]([CH:24]=[O:25])=[N:23][C:14]2=3)=[O:12])=[N:8][CH:9]=1)#[N:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118037151N-(5-cyanopyridin-2-yl)-2-(dimethoxymethyl)-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxamide2×

Product 1

HCID 118036674N-(5-cyanopyridin-2-yl)-2-formyl-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (0.65 ml) was added to a solution of N-(5-cyanopyridin-2-yl)-2-(dimethoxymethyl)-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxamide (intermediate 236, 29 mg, 0.079 mmol) in THF (0.9 ml) at room temperature. After stirring for 1 h at room temperature, sat. aq. NaHCO3 was added and the mixture extracted with DCM (3×). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was triturated with Et2O to give the title compound as a white solid.

Workup

  1. extractionthe mixture extracted with DCM (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-4a13d2d035f14a46b4bddc939c30000e
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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