Hydrochloric Acid → HCID 118036395, compound

HRID 1778116Notes

Reaction equation

HRID 1778116 reaction equation
[C:1]([C:3]1[C:4]([NH:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([N:27]4[CH2:31][CH2:30][CH:29]([CH3:32])[C:28]4=[O:33])=[C:19]([CH:22](OC)[O:23]C)[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2].Cl>C1COCC1.O>[C:1]([C:3]1[C:4]([NH:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([N:27]4[CH2:31][CH2:30][CH:29]([CH3:32])[C:28]4=[O:33])=[C:19]([CH:22]=[O:23])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118036313HCID 118036313, compound2×

Product 1

HCID 118036395HCID 118036395, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(3-methyl-2-oxopyrrolidin-1-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 330, 63 mg, 0.120 mmol) in THF (0.9 ml) and water (0.3 mL) was added 37% aqueous HCl (0.1 mL, 3.29 mmol) at room temperature and the reaction mixture was stirred for 4 h. The reaction mixture was quenched by the addition of saturated aqueous Na2CO3 and diluted with DCM. Phases were separated and the water phase was extracted with DCM. The combined organic layers were dried using Na2SO4, filtered and solvents were concentrated. The crude product was precipitated from DCM and EtOAc, filtered and dried to yield the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was quenched by the addition of saturated aqueous Na2CO3
  2. additiondiluted with DCM
  3. customPhases were separated
  4. extractionthe water phase was extracted with DCM
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationsolvents were concentrated
  8. customThe crude product was precipitated from DCM and EtOAc
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-6b6de2a858d64a10a8d659bdd7a6aa2a
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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