Trimethylsilyl isocyanate → HCID 10237179, compound

HRID 2306620Notes

Reaction equation

HRID 2306620 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[NH2:8][CH2:9][C@@H:10]1[O:14][C:13](=[O:15])[N:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[S:23][CH2:24][C:25](=[O:28])[NH:26][N:27]=3)=[C:18]([F:29])[CH:17]=2)[CH2:11]1>C1COCC1>[F:29][C:18]1[CH:17]=[C:16]([N:12]2[CH2:11][C@H:10]([CH2:9][NH:8][C:6]([NH2:5])=[O:7])[O:14][C:13]2=[O:15])[CH:21]=[CH:20][C:19]=1[C:22]1[S:23][CH2:24][C:25](=[O:28])[NH:26][N:27]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 23528997HCID 23528997, compound

Product 1

HCID 10237179HCID 10237179, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethylsilyl isocyanate (0.138 ml, 1.02 mmol) is added to a mixture of 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4] thiadiazin-5-one (0.30 g, 0.925 mmol) in THF (10 ml). The mixture is stirred at room temperature overnight and then is evaporated to dryness. The residue is purified by PTLC (10% MeOH/DCM) to give product as a white solid (0.22 g, 65%); 1HNMR (300 MHz, DMSO-d6) δ 3.29-3.36 (m, 2H), 3.59 (s, 2H), 3.78 (dd, J=6.3, 9.1 Hz, 1H), 4.13 (t, J=9.1 Hz, 1H), 4.69-4.77 (m, 1H), 5.58 (s, 1H), 6.31 (t, J=6.0 Hz, 1H), 7.42 (dd, J=2.2, 8.8 Hz, 1H), 7.59 (dd, J=2.2, 14 Hz, 1H), 7.68 (t, J=8.8 Hz, 1H), 11.6 (s, 1H); mp 235-6; MS (m/z): [M+H]+=368.

Workup

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

Sources & evidence

ORD record
ord-6b6ec623ae83449b8ec56ca8b41b9310
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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