Trifluoroacetic acid → HCID 18613518, compound

HRID 1265935Notes

Reaction equation

HRID 1265935 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([Cl:17])=[CH:10][C:9]=1[NH2:18])(C)(C)C.C(O[C:25](=[O:49])[CH2:26][C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]2[S:35][C:36]([CH2:39][CH2:40][O:41]C3CCCCO3)=[N:37][N:38]=2)[CH:29]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:17][C:11]1[C:12]([N:14]([CH3:16])[CH3:15])=[CH:13][C:8]2[N:7]=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]4[S:35][C:36]([CH2:39][CH2:40][OH:41])=[N:37][N:38]=4)[CH:29]=3)[CH2:26][C:25](=[O:49])[NH:18][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 69688689(2-Amino-4-chloro-5-dimethylamino-phenyl)-carbamic acid tert.-butyl esterHCID 69688856HCID 69688856, compound

Product 1

HCID 18613518HCID 18613518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from (2-amino-4-chloro-5-dimethylamino-phenyl)-carbamic acid tert.-butyl ester (Example J1) (0.15) and crude 3-oxo-3-(3-{5-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3,4]thiadiazol-2-yl}-phenyl)-propionic acid tert-butyl ester (0.24 g) (Example K30) according to the general procedure M. The obtained material was deprotected and cyclized by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as a yellow solid (0.10 g).

Sources & evidence

ORD record
ord-8a194d6714cc4949839cf203bceff6db
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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