Cyclopropanecarboxylic acid → HCID 10194166, compound

HRID 2306619Notes

Reaction equation

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

Participants

Reactant 2

HCID 15655Cyclopropanecarboxylic acid

HCID 23528997HCID 23528997, compound

Product 1

HCID 10194166HCID 10194166, compound

Procedure

Prepared from 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 and cyclopropanecarboxylic acid (0.0812 ml, 1.02 mmol) according to the method of Example 15 (0.30 g, 84%); 1HNMR (300 MHz, DMSO-d6) δ 0.59-0.68 (m, 4H), 1.53-1.62 (m, 1H), 3.44 (t, J=5.2 Hz, 2H), 3.58 (s, 2H), 3.72 (dd, J=6.3, 9.1 Hz, 1H), 4.14 (t, J=9.1 Hz, 1H), 4.72-4.78 (m, 1H), 7.41 (dd, J=2.2, 8.5 Hz, 1H), 7.53 (dd, J=2.2, 14 Hz, 1H), 7.68 (t, J=8.8 Hz, 1H), 8.46 (t, J=5.8 Hz, 1H), 11.6 (s, 1H); mp 239-40; MS (m/z): [M+H]+=393.

Sources & evidence

ORD record: ord-12e2e4d94693444caa9dfa19c6bc7d38
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828317B2

Reaction notes

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