Hydrochloric Acid → HCID 118036203, compound

HRID 1778079Notes

Reaction equation

HRID 1778079 reaction equation
C[O:2][CH:3](OC)[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)=[O:15])=[CH:6][C:5]=1[CH2:27][OH:28].O.Cl>C1COCC1>[CH:3]([C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)=[O:15])=[CH:6][C:5]=1[CH2:27][OH:28])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 1180362361,8-Naphthyridine-1(2H)-carboxamide, 7-(dimethoxymethyl)-3,4-dihydro-6-(hydroxymethyl)-N-[5-(trifluoromethyl)-2-pyridinyl]-2×

Product 1

HCID 118036203HCID 118036203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(dimethoxymethyl)-6-(hydroxymethyl)-N-(5-(trifluoromethyl)pyridin-2-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 14, 18 mg, 0.042 mmol) in THF (0.8 ml) was treated with water (0.6 ml) and conc. HCl (0.2 ml) and stirred for 15 min. The reaction mixture was quenched by addition of sat. aq. NaHCO3 (gas evolution), extracted with DCM (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was triturated with EtOAc/heptanes 10:1, filtered and dried under vacuum to give the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched by addition of sat. aq. NaHCO3 (gas evolution)
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was triturated with EtOAc/heptanes 10:1
  7. filtrationfiltered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-db35aec3cd9a46008ef53c4edec196d4
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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