3,3,3-Trifluoropropionyl chloride → 3,3,3-Trifluoro-1-(2-((3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)propan-1-one

HRID 604909Notes

Reaction equation

Cl.Cl.Cl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[S:20][C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:26]=3[N:27]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1.[F:28][C:29]([F:35])([F:34])[CH2:30][C:31](Cl)=[O:32]>>[F:28][C:29]([F:35])([F:34])[CH2:30][C:31]([N:23]1[CH2:24][CH2:25][C:26]2[N:27]=[C:19]([NH:18][C:8]3[CH:9]=[CH:10][C:11]([N:12]4[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]4)=[C:6]([O:5][CH3:4])[CH:7]=3)[S:20][C:21]=2[CH2:22]1)=[O:32]

Participants

Reactant 2

HCID 27833433,3,3-Trifluoropropionyl chloride

HCID 25106280N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine trihydrochloride

Product 1

HCID 251062833,3,3-Trifluoro-1-(2-((3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)propan-1-one

Procedure

The title compound was prepared in analogy to example 45 from 90 mg (0.2 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-amine trihydrochloride and 30 mg (0.2 mmol) 3,3,3-trifluoropropionylchloride yielding 29 mg (32%) 3,3,3-trifluoro-1-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl}-propan-1-one as a light yellow solid. MS ISP (m/e): 452.0 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.33 (s, 1H), 7.65 (S, 1 h), 7.47 (S, 1 h), 7.30-7.25 (m, 2H), 7.02 (s, 1H), 4.57 (br s, 2H), 3.85-3.59 (br m, 2H), 3.78 (s, 3H), 2.75 (m, 1H), 2.62 (m, 1H), 2.14 (s, 3H).

Sources & evidence

ORD record: ord-3b7f8587a87745a8a53f6f18a2f0f015
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910740B2

Reaction notes

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