(2R)-1-aminopropan-2-ol → HCID 69482703, compound

HRID 2364490Notes

Reaction equation

HRID 2364490 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:29])=[C:14]([C:24](OCC)=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:30][CH2:31][C@H:32]([OH:34])[CH3:33]>>[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:29])=[C:14]([C:24]([NH:30][CH2:31][C@H:32]([OH:34])[CH3:33])=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 439938(2R)-1-aminopropan-2-olHCID 69481032HCID 69481032, compound

Product 1

HCID 69482703HCID 69482703, compoundYield 25%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (60 mg, 0.15 mmol) and (2R)-1-amino-2-propanol (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2R)-2-hydroxypropyl]-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (16 mg, 25% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.02 (s, 1 H), 8.35 (s, 1 H), 7.56 (s, 1 H), 7.06-7.03 (m, 2 H), 6.89-6.84 (m, 2 H), 4.17 (m, 2 H), 4.01 (s, 2 H), 3.89 (m, 1 H), 3.45-3.39 (m, 3 H), 3.19 (m, 1 H),1.71 (m, 2 H), 1.09 (m, 3 H); MS m/z 430 (M+1).

Sources & evidence

ORD record
ord-90929a84e01246c9b81b9c05694a650f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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