Hydrochloric Acid → HCID 118036153, compound

HRID 1778094Notes

Reaction equation

HRID 1778094 reaction equation
Cl.[Si]([O:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[N:19][C:20]=1[CH:21](OC)[O:22]C)[N:17]([C:26]([NH:28][C:29]1[CH:34]=[C:33]([NH:35][CH2:36][C:37]([OH:40])([CH3:39])[CH3:38])[C:32]([C:41]#[N:42])=[CH:31][N:30]=1)=[O:27])[CH2:16][CH2:15][CH2:14]2)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1.O>[C:41]([C:32]1[C:33]([NH:35][CH2:36][C:37]([OH:40])([CH3:38])[CH3:39])=[CH:34][C:29]([NH:28][C:26]([N:17]2[C:18]3[C:13](=[CH:12][C:11]([CH2:10][OH:9])=[C:20]([CH:21]=[O:22])[N:19]=3)[CH2:14][CH2:15][CH2:16]2)=[O:27])=[N:30][CH:31]=1)#[N:42]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 131734801HCID 131734801, compound2×

Product 1

HCID 118036153HCID 118036153, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (0.17 ml) was added to a solution of 6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(5-cyano-4-((2-hydroxy-2-methylpropyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 78C, 30 mg, 0.051 mmol) in THF (1 ml) and water (0.5 ml) at room temperature. After stirring for 1 h at room temperature additional concentrated hydrochloric acid (0.17 ml) was added and stirring continued for a further 4.5 h. Saturated aqueous NaHCO3 was then added, the mixture extracted with DCM (2×), the organic layers dried over Na2SO4 and evaporated. The residue was purified by reversed phase preparative chromatography (RP 2) to give the title compound as a white solid.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with DCM (2×)
  3. dry with materialthe organic layers dried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by reversed phase preparative chromatography (RP 2)

Sources & evidence

ORD record
ord-fbad92c781564303a0af6ecd39db7d11
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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