HCID 69846637, compound → HCID 10194442, compound

HRID 2306614Notes

Reaction equation

HRID 2306614 reaction equation
FC(F)(F)C(O)=O.NC[C@@H]1OC(=O)N(C2C=CC(C3SC(CCO)C(=O)NN=3)=C(F)C=2)C1.[C:33]([NH:36][CH2:37][C@@H:38]1[O:42][C:41](=[O:43])[N:40]([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[S:51][CH:52]([CH2:57][CH2:58][O:59]C(=O)C)[C:53](=[O:56])[NH:54][N:55]=3)=[C:46]([F:63])[CH:45]=2)[CH2:39]1)(=[O:35])[CH3:34]>>[F:63][C:46]1[CH:45]=[C:44]([N:40]2[CH2:39][C@H:38]([CH2:37][NH:36][C:33](=[O:35])[CH3:34])[O:42][C:41]2=[O:43])[CH:49]=[CH:48][C:47]=1[C:50]1[S:51][CH:52]([CH2:57][CH2:58][OH:59])[C:53](=[O:56])[NH:54][N:55]=1

Participants

3

Reactant 2

HCID 69846637HCID 69846637, compoundHCID 131724683HCID 131724683, compound

Product 1

HCID 10194442HCID 10194442, compound

Procedure

Prepared from 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-6-(2-hydroxyethyl)-4H-[1,3,4]thiadiazin-5-one, trifluoroacetate salt according to the method of Example 2 (0.021 g, 31%). MS (m/z): [M+H]+=411. A second acetylation product is isolated and identified as acetic acid 2-(2-{4-[5(S)-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluorophenyl}-5-oxo-5,6-dihydro-4H[1,3,4]thiadiazin-6-yl)-ethyl ester (0.025 g, 37%); 1H NMR (300 MHz, DMSO-d6) δ 1.83-1.91 (m, 1H), 2.00 (s, 3H), 2.06-2.14 (m, 1H), 3.43 (t, J=5.4 Hz, 2H), 3.74-3.83 (m, 2H), 4.08-4.18 (m, 3H), 7.43 (dd, J=2.1, 8.7 Hz, 1H), 7.59 (dd, J=1.8, 13.5 Hz, 1H), 7.69 (t, J=8.7 Hz, 1H), 8.26 (t, J=5.7 Hz, 1H); mp 223-4; MS (m/z): [M+H]+=453.

Workup

  1. customA second acetylation product is isolated

Sources & evidence

ORD record
ord-4ddf9c7c4682420096e536a502337966
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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