Trifluoroacetic acid → HCID 86762164, compound

HRID 1907430Notes

Reaction equation

HRID 1907430 reaction equation
[F:1][CH:2]([F:37])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([F:36])=[C:17]([C@:19]34[O:27][CH2:26][CH2:25][C@H:24]3[CH2:23][S:22][C:21]([NH:28]C(=O)OC(C)(C)C)=[N:20]4)[CH:18]=2)=[O:11])=[N:8][CH:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C:21]1[S:22][CH2:23][C@@H:24]2[CH2:25][CH2:26][O:27][C@:19]2([C:17]2[CH:18]=[C:13]([NH:12][C:10](=[O:11])[C:7]3[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:37])[F:1])=[CH:9][N:8]=3)[CH:14]=[CH:15][C:16]=2[F:36])[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762165HCID 86762165, compound

Product 1

HCID 86762164HCID 86762164, compoundYield 145.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl ((4aR,7aR)-7a-(5-(5-(difluoromethoxy)picolinamido)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (6 mg, 0.011 mmol) and TFA (17.17 μL, 0.223 mmol) in DCM (111 μL) was stirred at rt for 3 h, and the solvents were removed to give N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-(difluoromethoxy)picolinamide (7 mg) as its TFA salt as a colorless oil. 1H NMR (500 MHz, METHANOL-d4) 8.60 (br. s., 1H), 8.29 (br. s., 1H), 8.18 (dd, J=7.1, 2.7 Hz, 1H), 7.94-7.87 (m, 1H), 7.84 (dd, J=8.6, 1.6 Hz, 1H), 7.31-7.22 (m, 1H), 7.10 (t, J=75 Hz, 1H), 4.33-4.19 (m, 2H), 3.46 (dd, J=13.6, 3.8 Hz, 1H), 3.34-3.25 (m, 1H), 3.18-3.09 (m, 1H), 2.32 (q, J=7.0 Hz, 2H). MS (M+H)+: 439.11.

Workup

  1. customthe solvents were removed

Sources & evidence

ORD record
ord-593d518510404da88a651a1dfc0930fb
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

Loading…