HCID 10007590, compound → HCID 10392661, compound

HRID 1725352Notes

Reaction equation

HRID 1725352 reaction equation
[OH:1][C@H:2]([CH2:19][N:20]1[CH2:24][C@@H:23]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[N:33]=3)[N:28]=[CH:27][CH:26]=2)[O:22][C:21]1=[O:37])[CH2:3][NH:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]2[S:16][CH2:15][C:14](=[O:17])[NH:13][C:12]=2[CH:18]=1)(=[O:7])=[O:6].CC1(C)O[C@H](CN)CO1>>[OH:1][C@@H:2]([CH2:19][N:20]1[CH2:24][C@@H:23]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[N:33]=3)[N:28]=[CH:27][CH:26]=2)[O:22][C:21]1=[O:37])[CH2:3][NH:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]2[S:16][CH2:15][C:14](=[O:17])[NH:13][C:12]=2[CH:18]=1)(=[O:6])=[O:7]

Participants

3

Reactant 2

HCID 10007590HCID 10007590, compoundHCID 101540731-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methanamine

Product 1

HCID 10392661HCID 10392661, compound

Procedure

The title compound was prepared using the same procedure as 3-Oxo-3,4-dihydro-2H benzo[1,4]thiazine-6-sulfonic acid {(R)-2-hydroxy-3-[(R)-5-(6-methoxy-[1,5]naphthyridin-4-yl)-2-oxo-oxazolidin-3-yl]-propyl}-amide (GSK-203344A) except substituting C-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methylamine for C-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methylamine. 1H NMR (400 MHz, CDCl3): δ8.72 (d, J=4.5 Hz, 1H); 8.19 (d, J=9.1 Hz, 1H); 7.59 (d, J=4.6 Hz, 1H); 7.35-7.42 (overlapping signals (3H); 7.11 (d, J=9.1 Hz, 1H); 6.30 (m, 1H); 4.54 (t, J=9.4 Hz, 1H); 4.01-4.08 (m, 1H); 3.99 (s, 3H); 3.58 (dd, J=8.8, 7.5 Hz, 1H); 3.49 (dd, J=14.6, 7.0 Hz, 1H); 3.44 (s, 2H); 3.27 (dd, J=14.7, 3:6 Hz, 1H); 3.08 (dd, J=13.4, 3.8 Hz, 1H); 2.99 (dd, J=13.1, 6.3 Hz, 1H); 2.62 (m, 1H). MS (ES) m/e 546 (M+H)+.

Sources & evidence

ORD record
ord-0e4b477d8be440828699b2159026dce0
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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