Hydrochloric Acid → HCID 118036347, compound

HRID 1778089Notes

Reaction equation

HRID 1778089 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[N:18][C:19]=1[CH:20](OC)[O:21]C)[N:16]([C:25]([NH:27][C:28]1[N:33]=[C:32]([O:34][C@H:35]3[CH2:39][CH2:38][O:37][CH2:36]3)[C:31]([C:40]#[N:41])=[CH:30][N:29]=1)=[O:26])[CH2:15][CH2:14][CH2:13]2)(C(C)(C)C)(C)C.Cl>C1COCC1.O>[C:40]([C:31]1[C:32]([O:34][C@H:35]2[CH2:39][CH2:38][O:37][CH2:36]2)=[N:33][C:28]([NH:27][C:25]([N:16]2[C:17]3[C:12](=[CH:11][C:10]([CH2:9][OH:8])=[C:19]([CH:20]=[O:21])[N:18]=3)[CH2:13][CH2:14][CH2:15]2)=[O:26])=[N:29][CH:30]=1)#[N:41]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131734800HCID 131734800, compound2×

Product 1

HCID 118036347HCID 118036347, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(5-cyano-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 37Q, 76 mg, 0.13 mmol) was dissolved in THF (2 ml) and water (1 ml), treated with conc. HCl (0.5 ml) and stirred for 16 h at room temperature. The reaction mixture was quenched with sat. aq. NaHCO3 and extracted with DCM (3×). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by preparative supercritical fluid chromatography (SFC 1, 4EP column) to give the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched with sat. aq. NaHCO3
  2. extractionextracted with DCM (3×)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by preparative supercritical fluid chromatography (SFC 1, 4EP column)

Sources & evidence

ORD record
ord-c3d15a17c6444946934878bd9e49007d
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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