Trifluoroacetic acid → HCID 11742633, compound

HRID 2415297Notes

Reaction equation

HRID 2415297 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[S:20][C:21]([C:25](=[O:35])[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([F:34])[CH:27]=3)=[C:22]([NH2:24])[N:23]=2)=[CH:14][CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:24][C:22]1[N:23]=[C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][NH2:7])=[CH:13][CH:14]=2)[S:20][C:21]=1[C:25]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([F:34])[CH:27]=1)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23525779HCID 23525779, compound

Product 1

HCID 11742633HCID 11742633, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-[4-[4-Amino-5-(3-fluoro-4-methoxy-benzoyl)-thiazol-2-ylamino]-phenoxy]-propyl)-carbamic acid tert-butyl ester (254 mg) (from Step A above) in dichloromethane (6 mL) at 0° C. was added trifluoroacetic acid (3 mL). After stirring for 1 hour, the mixture was concentrated and the residue was purified on HPLC to give [4-Amino-2-[4-(3-aminopropoxy)-phenylamino]-thiazol-5-yl]-(3-fluoro-4-methoxy-phenyl)-methanone (180.9 mg, 88% yield) as a light yellow solid. HRMS, Observed: 417.1394; Calcd for M+H+: 417.1391.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified on HPLC

Sources & evidence

ORD record
ord-1e7ab9e7480445aa9c00eb0b163cf685
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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