1-Amino-2-propanol → HCID 69482038, compound

HRID 2364399Notes

Reaction equation

HRID 2364399 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][CH: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][CH: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 41-Amino-2-propanolHCID 69481032HCID 69481032, compound

Product 1

HCID 69482038HCID 69482038, compoundYield 34%

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, 0.15mmol) and 1-amino-2-propanol (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (22 mg, 34% yield) as a yellow solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.27 (br s, 1 H), 8.49 (s, 1 H), 7.52 (s, 1 H), 7.14-7.10 (m, 2 H), 6.99-6.94 (m, 2 H), 4.26 (m, 2 H), 4.09 (s, 2 H), 3.95 (m, 1 H), 3.55-3.47 (m, 3 H), 3.29 (m, 1 H), 1.79 (m, 2 H), 1.19 (d, J=6 Hz, 3 H); MS m/z 430 (M+1).

Sources & evidence

ORD record
ord-adb42926eddf4757906791f391f13095
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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