Hydrochloric Acid → HCID 118036782, compound

HRID 1778095Notes

Reaction equation

HRID 1778095 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:43])([CH3:42])[CH2:38][N:39]([CH3:41])[CH3:40])[C:32]([C:44]#[N:45])=[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:44]([C:32]1[C:33]([NH:35][CH2:36][C:37]([OH:43])([CH3:42])[CH2:38][N:39]([CH3:40])[CH3:41])=[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:45]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131734802HCID 131734802, compound2×

Product 1

HCID 118036782HCID 118036782, 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-((3-(dimethylamino)-2-hydroxy-2-methylpropyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 78D, 33 mg, 0.053 mmol) in THF (1 ml) and water (0.5 ml) at room temperature. After stirring for 18 h at room temperature saturated aqueous NaHCO3 was then added, the mixture extracted with DCM (2×), the organic layers dried over Na2SO4 and evaporated. The residue was triturated with Et2O to give the title compound.

Workup

  1. additionwas then added
  2. extractionthe mixture extracted with DCM (2×)
  3. dry with materialthe organic layers dried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-7be62aecf90e44aa970fe286d7d61aed
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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