Acetic Anhydride → HCID 10126433, compound

HRID 2306613Notes

Reaction equation

HRID 2306613 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[NH2:8][CH2:9][CH:10]1[O:14][C:13](=[O:15])[N:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[S:23][CH:24]([CH3:29])[C:25](=[O:28])[NH:26][N:27]=3)=[C:18]([F:30])[CH:17]=2)[CH2:11]1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[F:30][C:18]1[CH:17]=[C:16]([N:12]2[CH2:11][C@H:10]([CH2:9][NH:8][C:3](=[O:4])[CH3:2])[O:14][C:13]2=[O:15])[CH:21]=[CH:20][C:19]=1[C:22]1[S:23][C@@H:24]([CH3:29])[C:25](=[O:28])[NH:26][N:27]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 131724682HCID 131724682, compound

Product 1

HCID 10126433HCID 10126433, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[4-(5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-6-methyl-4H-[1,3,4]thiadiazin-5-one, trifluoroacetate salt is dissolved in pyridine (2 ml) and acetic anhydride (0.0163 ml, 0.173 mmol) is added. The reaction is stirred at room temperature for 4 hours and then evaporated to dryness. The residue is purified by PTLC (10% MeOH/DCM) to give pure product as a white solid (0.046 g, 76%); 1HNMR (300 MHz, DMSO-d6) δ 1.34 (d, J=7.1 Hz, 3H), 1.82 (s, 3H), 3.41 (t, J=5.5, 2H), 3.71-3.82 (m, 2H), 4.14 (t, J=9.3 Hz, 1H), 4.71-4.79 (m, 1H), 7.41 (dd, J=1.9, 8.8 Hz, 1H), 7.58 (dd, J=1.7, 14, 1H), 7.68 (t, J=8.5, 1H), 8.25 (t, J=5.5 Hz, 1H), 11.7 (s, 1H); mp 200-2; MS (m/z): [M+H]+=381.

Workup

  1. customevaporated to dryness
  2. customThe residue is purified by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-fff1c8043a294bcd8e6a8e7813be442d
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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