Trifluoroacetic acid → HCID 86762166, compound

HRID 1907431Notes

Reaction equation

HRID 1907431 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][C:3]=1[C@:18]12[O:26][CH2:25][CH2:24][C@H:23]1[CH2:22][S:21][C:20]([NH:27]C(=O)OC(C)(C)C)=[N:19]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][C:20]1[S:21][CH2:22][C@@H:23]2[CH2:24][CH2:25][O:26][C@:18]2([C:3]2[CH:4]=[C:5]([NH:8][C:9](=[O:17])[C:10]3[C:15]([F:16])=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:6]=[CH:7][C:2]=2[F:1])[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762167HCID 86762167, compound

Product 1

HCID 86762166HCID 86762166, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl ((4aR,7aR)-7a-(2-fluoro-5-(3-fluoropicolinamido)phenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (6 mg, 0.012 mmol) and TFA (18.85 μL, 0.245 mmol) in DCM (122 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)-3-fluoropicolinamide (7 mg) as its TFA salt as a colorless oil. 1H NMR (500 MHz, METHANOL-d4) δ 8.84-8.37 (br. s, 2H), 8.17 (dd, J=7.2, 2.3 Hz, 1H), 7.92-7.76 (m, 2H), 7.26 (dd, J=11.1, 8.9 Hz, 1H), 4.37-4.19 (m, 2H), 3.46 (dd, J=13.6, 3.8 Hz, 1H), 3.35-3.25 (m, 1H), 3.19-3.04 (m, 1H), 2.32 (q, J=7.0 Hz, 2H). MS (M+H)+: 391.10.

Workup

  1. customthe solvents were removed

Sources & evidence

ORD record
ord-6609698ef6ce47a8a50b1cccad5c83dd
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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