Methyl carbazate → 1-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyridin-2(1H)-one monohydrochloride

HRID 1022762Notes

Reaction equation

[C:1]([C:4]1[C:5](=[O:33])[N:6]([CH2:10][C@H:11]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=3)[O:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)[CH:7]=[CH:8][CH:9]=1)(=S)[NH2:2].[C:34]([O:38]C)(=O)[NH:35][NH2:36]>>[ClH:24].[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C@@H:17]2[O:16][CH2:15][CH2:14][NH:13][CH2:12][C@H:11]2[CH2:10][N:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1]3[NH:2][C:34](=[O:38])[NH:35][N:36]=3)[C:5]2=[O:33])=[CH:19][C:20]=1[F:25]

Participants

Reactant 2

HCID 80519Methyl carbazate

HCID 86663873tert-butyl (6R,7R)-6-[(3-carbamothioyl-2-oxopyridin-1(2H)-yl)methyl]-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 1363407021-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyridin-2(1H)-one monohydrochloride

Procedure

Using tert-butyl (6R,7R)-6-[(3-carbamothioyl-2-oxopyridin-1(2H)-yl)methyl]-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate and methyl carbazate, and in the same manner as in Example 200, the title compound was obtained.

Sources & evidence

ORD record: ord-bc0e855987cb4b478b4068a25e0970c9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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