Trifluoroacetic acid → HCID 86762161, compound

HRID 1907428Notes

Reaction equation

HRID 1907428 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[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[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]=3)[CH:6]=[CH:7][C:2]=2[F:1])[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762151HCID 86762151, compound

Product 1

HCID 86762161HCID 86762161, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl ((4aR,7aR)-7a-(2-fluoro-5-(5-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. 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-fluoropicolinamide (7 mg) as its TFA salt. 1H NMR (500 MHz, CHLOROFORM-d) δ 9.83 (s, 1H), 8.48 (d, J=2.7 Hz, 1H), 8.35 (dd, J=8.7, 4.6 Hz, 1H), 8.00-7.96 (m, 1H), 7.70 (dd, J=6.9, 2.7 Hz, 1H), 7.62 (td, J=8.3, 2.7 Hz, 1H), 7.08 (dd, J=10.9, 8.8 Hz, 1H), 4.11 (t, J=7.2 Hz, 3H), 3.16 (dd, J=13.0, 4.0 Hz, 1H), 2.98 (ddd, J=12.9, 7.5, 1.8 Hz, 1H), 2.78 (dd, J=7.1, 4.0 Hz, 1H), 2.22-1.99 (m, 2H). MS (M+H)+: 391.2.

Workup

  1. customThe solvents were removed

Sources & evidence

ORD record
ord-02f7645446d74d8c9099fda0cc1af886
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

Loading…