Triethylamine → HCID 10194416, compound

HRID 2306621Notes

Reaction equation

HRID 2306621 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][CH2:8][C@@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=3)=[C:17]([F:28])[CH:16]=2)[CH2:10]1.C(N(CC)CC)C>CN(C=O)C>[F:28][C:17]1[CH:16]=[C:15]([N:11]2[CH2:10][C@H:9]([CH2:8][NH:7][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])[O:13][C:12]2=[O:14])[CH:20]=[CH:19][C:18]=1[C:21]1[S:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 23528997HCID 23528997, compound

Product 1

HCID 10194416HCID 10194416, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diketene (0.0590 ml, 0.648 mmol) is added dropwise to a solution of 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.200 g, 0.617 mmol) and triethylamine (0.0946 ml, 0.679 mmol) in DMF (2 ml) and is stirred overnight at room temperature. The reaction mixture is evaporated to dryness and the residue is purified by PTLC (10% MeOH/DCM) to give a white solid (0.22 g, 89%); 1HNMR (300 MHz, DMSO-d6) δ 2.08 (s, 3H), 3.34 (s, 2H), 3.42-3.54 (m, 2H), 3.59 (s, 2H), 3.78 (dd, J=6.3, 9.1 Hz, 1H), 4.14 (t, J=9.1 Hz, 1H), 4.75-4.83 (m, 1H), 7.37 (dd, J=2.2, 8.5 Hz, 1H), 7.52 (dd, J=2.2, 14 Hz, 1H), 7.69 (t, J=8.8 Hz, 1H), 8.45 (t, J=5.8 Hz, 1H), 11.6 (s, 1H); mp 176-8; MS (m/z): [M+H]+=409.

Workup

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

Sources & evidence

ORD record
ord-96b784054882424196e98db6875d670f
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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