Trifluoroacetic acid → HCID 67777623, compound

HRID 1026271Notes

Reaction equation

C([O:8][C:9]1[CH:31]=[CH:30][C:12]2[N:13]=[C:14]([C:16]3[CH:29]=[CH:28][C:19]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:27])[CH3:26])[CH3:23])=[CH:18][CH:17]=3)[S:15][C:11]=2[CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1>>[OH:8][C:9]1[CH:31]=[CH:30][C:12]2[N:13]=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:27])[CH3:26])[CH3:23])=[CH:28][CH:29]=3)[S:15][C:11]=2[CH:10]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7520Thioanisole

HCID 67778339HCID 67778339, compound

Product 1

HCID 67777623HCID 67777623, compoundYield 106%

Conditions

Temperature: 55 °C

Procedure

A mixture of N-[(1S)-2-{4-[6-(benzyloxy)-1,3-benzothiazol-2-yl]phenoxy}-1-methylethyl]acetamide (46 mg), trifluoroacetic acid (1 mL) and thioanisole (0.1 mL) was stirred at 55° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with diisopropyl ether to give N-{(1S)-2-[4-(6-hydroxy-1,3-benzothiazol-2-yl)phenoxy]-1-methylethyl}acetamide (38.6 mg) as a powder. Using the obtained powder, and in the same manner as in Example 1, step A, the title compound was obtained.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record: ord-4b0aade0f90f49cca12363e449f50bfc
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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