Methylamine → HCID 59558815, compound

HRID 1175377Notes

Reaction equation

HRID 1175377 reaction equation
C(OC(=O)[C@H](O[C:8]1C=C(Cl)N=C(SCC2C=CC=C(F)C=2F)[N:9]=1)C)C.C([O:28][C:29](=O)[C@H:30]([O:32][C:33]1[CH:38]=[C:37]([NH:39][S:40]([N:43]2[CH2:46][CH2:45][CH2:44]2)(=[O:42])=[O:41])[N:36]=[C:35]([S:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([F:55])[C:50]=2[F:56])[N:34]=1)[CH3:31])C.CN>C(O)C>[N:43]1([S:40]([NH:39][C:37]2[N:36]=[C:35]([S:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([F:55])[C:50]=3[F:56])[N:34]=[C:33]([O:32][C@H:30]([CH3:31])[C:29]([NH:9][CH3:8])=[O:28])[CH:38]=2)(=[O:41])=[O:42])[CH2:44][CH2:45][CH2:46]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 59558764HCID 59558764, compoundHCID 866198702-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy](2R)-propanoic acid ethyl ester

Product 1

HCID 59558815HCID 59558815, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester (the product of example 23) (100 mg) in ethanol (1.5 mL) was added 8M methylamine in ethanol. The resulting mixture was stirred in a sealed tube at ambient temperature for 166 h. The solvent was evaporated under reduced pressure. Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase) to give the title compound as a white solid. Yield: 60 mg MS: APCI (+ve) 474 [M+H+]

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customPurification

Sources & evidence

ORD record
ord-00eb550dd94847d6bf07ab7c463bc44c
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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