Hydrochloric Acid → HCID 71087114, compound

HRID 571834Notes

Reaction equation

HRID 571834 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[CH:26][C:25]=3[O:32][CH3:33])=[O:22])=[C:16]([F:34])[CH:15]=2)[CH2:9]1)=O)(C)(C)C.[ClH:35].O1CCOCC1>C1COCC1>[ClH:35].[C:30]([C:28]1[CH:27]=[CH:26][C:25]([O:32][CH3:33])=[C:24]([NH:23][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([C@@H:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:15][C:16]=2[F:34])=[O:22])[CH:29]=1)#[N:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71086965HCID 71086965, compound

Product 1

HCID 71087114HCID 71087114, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-2-{4-[3-(5-Cyano-2-methoxy-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester (97 mg, 106 μmol, Eq: 1.00) in THF (4 ml) was added 4M−HCl in dioxane (0.773 ml, 3.09 mmol, Eq: 15). The reaction mixture was stirred at 60° C. for 5 h. To the cooled mixture was then added ethyl acetate and the suspension was filtered off and dried under high vacuo to give the target compound as an off-white solid (63 mg, 75%). MS (ISP): 369.1 ([M+H]+).

Workup

  1. filtrationadded ethyl acetate and the suspension was filtered off
  2. customdried under high vacuo

Sources & evidence

ORD record
ord-7b0f6c9ed4244470a4ef8a5624791066
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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