Hydrochloric Acid → HCID 118036257, compound

HRID 1778114Notes

Reaction equation

HRID 1778114 reaction equation
Cl.[C:2]([C:4]1[C:5]([NH:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[C:20]([CH:23](OC)[O:24]C)[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:8][CH:9]=1)#[N:3].C([O-])(O)=O.[Na+]>C1COCC1.O>[C:2]([C:4]1[C:5]([NH:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)=[C:20]([CH:23]=[O:24])[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:8][CH:9]=1)#[N:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118036402HCID 118036402, compound2×

Product 1

HCID 118036257HCID 118036257, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (0.28 ml) was added to a solution of N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(tetrahydro-2H-pyran-4-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 310, 640 mg, 0.689 mmol) in THF (6 ml) and water (2 ml) at room temperature. After stirring for 4 h at room temperature saturated aqueous NaHCO3 was added, the mixture extracted with DCM, the organic layers dried over MgSO4 and evaporated. The residue was triturated with EtOAc and then filtered to give the title compound as a white solid.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with DCM
  3. dry with materialthe organic layers dried over MgSO4
  4. customevaporated
  5. customThe residue was triturated with EtOAc
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f2b9393176ab4ddcaa4c3189af48a95f
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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