Hydrochloric Acid → HCID 118036949, compound

HRID 1778103Notes

Reaction equation

HRID 1778103 reaction equation
Cl.[C:2]([C:4]1[C:5]([NH:31][CH2:32][CH:33]2[O:38][CH2:37][CH2:36][N:35]([CH3:39])[CH2:34]2)=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]([F:30])[F:29])=[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>[C:2]([C:4]1[C:5]([NH:31][CH2:32][CH:33]2[O:38][CH2:37][CH2:36][N:35]([CH3:39])[CH2:34]2)=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH:28]([F:30])[F:29])=[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118036703HCID 118036703, compound2×

Product 1

HCID 118036949HCID 118036949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrochloric acid (4 M, 3.5 ml) was added to a solution of (racemic) N-(5-cyano-4-(((4-methylmorpholin-2-yl)methyl)amino)pyridin-2-yl)-6-(difluoromethyl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 232B, 55 mg, 0.103 mmol) in THF (2 ml) at room temperature. After stirring for 2 h at room temperature, sat. aq. NaHCO3 was added and the mixture extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was triturated and sonicated with DCM to give the title compound. (UPLC-MS 3) tR 0.79 min; MS m/z [M+H]+ 486.4.

Workup

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

Sources & evidence

ORD record
ord-d3341dc6db3d46bf85d9676227165bdc
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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