Trifluoroacetic acid → HCID 66745945, compound

HRID 1467277Notes

Reaction equation

HRID 1467277 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C@@H:16]3[C@@H:20]([OH:21])[C@@H:19]([OH:22])[CH:18]([OH:23])[O:17]3)=[CH:12][CH:11]=[CH:10][C:4]=2[NH:5][S:6](=[O:9])(=[O:8])[N:7]=1.F[C:25](F)(F)C(O)=O>CO>[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C@@H:16]3[C@@H:20]([OH:21])[C@@H:19]([OH:22])[CH:18]([O:23][CH3:25])[O:17]3)=[CH:12][CH:11]=[CH:10][C:4]=2[NH:5][S:6](=[O:8])(=[O:9])[N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66746582HCID 66746582, compound

Product 1

HCID 66745945HCID 66745945, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-Amino-5-(((2R,3S,4R)-3,4,5-trihydroxytetrahydrofuran-2-yl)methoxy)-1H-benzo[c][1,2,6]thiadiazine-2,2-dioxide (Example 212a) (7 mg, 0.020 mmol) in dry methanol (1 mL) was added trifluoroacetic acid 0.2 mL) and the mixture was refluxed overnight. The resulting solution was evaporated to dryness to provide the title compound as a white powder (7.28 mg, 100%, mixture of diastereomers˜4/1). 1H NMR (400 MHz, DMSO-d6): δ0 [3.17 (s, ¾H)], 3.22 (s, 3H), 3.81 (d, J=4.0 Hz, 1H), [3.93 (m, ½H)], 4.12 (m, 3H), 4.39 (m, 1H), 4.71 (s, 1H), [4.85 (d, J=4.0 Hz, ¼H)], 5.44 (br s, 2H), 6.65 (d, J=8.0 Hz, 1H), 6.81 (d, J=8.0 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 7.95 (s, 1H), 8.41 (s, 1H), 11.00 (s, 1H), [11.01 (s, ¼H)].

Workup

  1. temperaturewas refluxed overnight
  2. customThe resulting solution was evaporated to dryness

Sources & evidence

ORD record
ord-1de4101b794e4478b81a19210d36fc68
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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