Trifluoroacetic acid → HCID 22317657, compound

HRID 498859Notes

Reaction equation

HRID 498859 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.C([O:15][C:16](=O)[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[CH:31]=[C:30]([CH2:32][O:33]C3CCCCO3)[N:29]=[C:28]([CH3:40])[CH:27]=2)[CH:21]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C1(C)C(C)=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:16](=[O:15])[CH2:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4[CH:27]=[C:28]([CH3:40])[N:29]=[C:30]([CH2:32][OH:33])[CH:31]=4)[CH:21]=3)=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 69489452(RS)-3-{3-[2-Methyl-6-(tetrahydro-pyran-2-yloxymethyl)-pyridin-4-yl]-phenyl}-3-oxo-propionic acid tert-butyl ester

Product 1

HCID 22317657HCID 22317657, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Procedure

The title compound was prepared from commercially available 4,5-dichloro-1,2-phenylendiamine (177 mg, 1.0 mmol) and (RS)-3-{3-[2-methyl-6-(tetrahydro-pyran-2-yloxymethyl)-pyridin-4-yl]-phenyl}-3-oxo-propionic acid tert-butyl ester (Example K64) (426 mg, 1.0 mmol) in xylene (20 ml) under reflux conditions for 1.5 h according to the general procedure M and subsequent treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as a light brown solid (140 mg, 35%).

Sources & evidence

ORD record
ord-d8b128ff6105444d9ac93d537005a0a9
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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