1-Amino-2-propanol → HCID 69482841, compound

HRID 2364298Notes

Reaction equation

HRID 2364298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:32])=[C:14]([C:27](OCC)=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:33][CH2:34][CH:35]([OH:37])[CH3:36]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:32])=[C:14]([C:27]([NH:33][CH2:34][CH:35]([OH:37])[CH3:36])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 69480155HCID 69480155, compound

Product 1

HCID 69482841HCID 69482841, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylsulfonyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 1-amino-2-propanol employing methods similar to those described in Example 202 and was obtained as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.33 (t, J=5.1 Hz, 1 H), 8.56 (s, 1 H), 7.67 (s, 1 H), 7.21 (dd, J=8.2, 5.4 Hz, 2 H), 7.01 (t, J=8.5 Hz, 2 H), 4.37 (t, J=7.7 Hz, 2 H), 4.12 (s, 2 H), 4.08 (m, 2 H), 3.62 (m, 1 H), 3.35 (m, 1 H), 3.14 (t, J=6.7 Hz, 2 H), 2.95 (s, 3 H), 2.19 (m, 2 H), 1.27 (d, J=6.4 Hz, 3 H); HRMS C23H26FN3O6S (M+H)+ calcd 492.1526, found 492.1623.

Workup

  1. customwas obtained as a pale yellow solid

Sources & evidence

ORD record
ord-86f918ec8cad4fc697857242930745fc
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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