Hydrochloric Acid → HCID 23652997, compound

HRID 1094532Notes

Reaction equation

HRID 1094532 reaction equation
Cl.[C:2]([NH:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:19]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]4[CH2:37][CH2:36][CH2:35][C@H:34]([NH:38]C(=O)OC(C)(C)C)[CH2:33]4)=[C:28]([C:46]([F:49])([F:48])[F:47])[CH:27]=2)=[O:24])=[CH:18][CH:17]=[CH:16]3)[CH:7]=1)(=[O:4])[CH3:3].C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:38][C@H:34]1[CH2:35][CH2:36][CH2:37][N:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:23]([C:19]3[C:20]4[C:15](=[CH:14][C:13]([O:12][C:8]5[CH:7]=[C:6]([NH:5][C:2](=[O:4])[CH3:3])[N:11]=[CH:10][N:9]=5)=[CH:22][CH:21]=4)[CH:16]=[CH:17][CH:18]=3)=[O:24])=[CH:27][C:28]=2[C:46]([F:49])([F:48])[F:47])[CH2:33]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23653138HCID 23653138, compound

Product 1

HCID 23652997HCID 23652997, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.3 ml hydrogen chloride (4 M in dioxane) is added to a stirred solution of 0.24 g (0.38 mmol) [(3S)-1-[4-[[[6-(6-acetylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]carbonyl-]-amino]-2-(trifluoromethyl)phenyl]-3-piperidinyl]-carbamic acid, 1,1-dimethylethyl ester (Ex. 35) in 2.3 ml dioxan at room temperature. After 90 min, the mixture is poured into an excess of saturated aqueous NaHCO3. The crude product is filtered and purified by chromatography (SiO2, CH2Cl2/EtOH/NH3 90:9:1) to afford the title compound as a beige solid: m.p.: 218-228° C.

Workup

  1. filtrationThe crude product is filtered
  2. custompurified by chromatography (SiO2, CH2Cl2/EtOH/NH3 90:9:1)

Sources & evidence

ORD record
ord-3f878618860648c7b51d4be81010cc2b
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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