Trifluoroacetic acid → N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-cyanopicolinamide

HRID 1907427Notes

Reaction equation

HRID 1907427 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([F:35])=[C:16]([C@:18]34[O:26][CH2:25][CH2:24][C@H:23]3[CH2:22][S:21][C:20]([NH:27]C(=O)OC(C)(C)C)=[N:19]4)[CH:17]=2)=[O:10])=[N:7][CH:8]=1)#[N: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:16]2[CH:17]=[C:12]([NH:11][C:9](=[O:10])[C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH:13]=[CH:14][C:15]=2[F:35])[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762150HCID 86762150, compound

Product 1

HCID 86762160N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-cyanopicolinamideYield 146.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl ((4aR,7aR)-7a-(5-(5-cyanopicolinamido)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (6 mg, 0.012 mmol) and TFA (18.58 μL, 0.241 mmol) in DCM (121 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-cyanopicolinamide (7 mg) as its TFA salt as a colorless oil. 1H NMR (500 MHz, CD3OD) δ 9.07 (1H, s), 8.46 (1H, dd, J=2.0, 8.0 Hz0, 8.37 (1H, d, J=8.0 Hz0, 8.17 (1H, dd, J=3.0, 7.5 Hz), 7.93 (1H, m), 7.25 (1H, dd, J=9.0, 11.0 Hz), 4.23 (2H, m), 3.43 (1H, m), 3.29 (1H, m), 3.15 (1H, m), and 2.31 (2H, m). MS (M+H)+: 398.1.

Workup

  1. customThe solvents were removed

Sources & evidence

ORD record
ord-f163fc68661f4a98847a1a427786b7d7
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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