Hydrochloric Acid → (racemic) N-(5-cyano-4-(2-((dimethylamino)methyl)morpholino)pyridin-2-yl)-7-formyl-6-(hydroxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1778091Notes

Reaction equation

HRID 1778091 reaction equation
Cl.[Si]([O:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[N:19][C:20]=1[CH:21](OC)[O:22]C)[N:17]([C:26]([NH:28][C:29]1[CH:34]=[C:33]([N:35]3[CH2:40][CH2:39][O:38][CH:37]([CH2:41][N:42]([CH3:44])[CH3:43])[CH2:36]3)[C:32]([C:45]#[N:46])=[CH:31][N:30]=1)=[O:27])[CH2:16][CH2:15][CH2:14]2)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1>[C:45]([C:32]1[C:33]([N:35]2[CH2:40][CH2:39][O:38][CH:37]([CH2:41][N:42]([CH3:44])[CH3:43])[CH2:36]2)=[CH:34][C:29]([NH:28][C:26]([N:17]2[C:18]3[C:13](=[CH:12][C:11]([CH2:10][OH:9])=[C:20]([CH:21]=[O:22])[N:19]=3)[CH2:14][CH2:15][CH2:16]2)=[O:27])=[N:30][CH:31]=1)#[N:46]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131734785(racemic) 6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(5-cyano-4-(2-((dimethylamino)methyl)morpholino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide2×

Product 1

HCID 118036864(racemic) N-(5-cyano-4-(2-((dimethylamino)methyl)morpholino)pyridin-2-yl)-7-formyl-6-(hydroxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous hydrochloric acid (3 M, 1 ml) was added to a solution of 6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(5-cyano-4-(2-((dimethylamino)methyl)morpholino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 76, 168 mg, 0.262 mmol) in THF (1.6 ml) at room temperature. After stirring for 1 h saturated aqueous NaHCO3 was added, the mixture extracted with DCM (3×), the organic layers dried over Na2SO4 and evaporated. The residue was sonicated with EtOAc (2 ml) and hexanes (3 ml) and then filtered to give the title compound as a white solid.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with DCM (3×)
  3. dry with materialthe organic layers dried over Na2SO4
  4. customevaporated
  5. customThe residue was sonicated with EtOAc (2 ml) and hexanes (3 ml)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6b7cedd740944caaa07d459b2deed09f
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…