Trifluoroacetic acid → HCID 10343422, compound

HRID 2415299Notes

Reaction equation

HRID 2415299 reaction equation
C(OC(=O)[N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[S:22][C:23]([C:27](=[O:37])[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([F:36])[CH:29]=3)=[C:24]([NH2:26])[N:25]=2)=[CH:16][CH:15]=1)[CH2:8][CH3:9])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:26][C:24]1[N:25]=[C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][CH2:10][NH:7][CH2:8][CH3:9])=[CH:15][CH:16]=2)[S:22][C:23]=1[C:27]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([F:36])[CH:29]=1)=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23525780HCID 23525780, compound

Product 1

HCID 10343422HCID 10343422, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-[4-[4-Amino-5-(3-fluoro-4-methoxybenzoyl)-thiazol-2-ylamino]-phenoxy]-propyl)-ethyl-carbamic acid tert-butyl ester (220.5 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 [4-Amino-2-[4-(3-ethylamino-propoxy)-phenylamino]-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)-methanone (159.8 mg, 89% yield) as a light yellow solid. HRMS, observed: 445.1707; Calcd for M+H: 445.1704.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-099125ce5ee64e83a1c6c88eac13c1e0
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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