2-Amino-2-methyl-1-propanol → HCID 69482668, compound

HRID 2364303Notes

Reaction equation

HRID 2364303 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:25])=[C:14]([C:20](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:26][C:27]([CH3:31])([CH3:30])[CH2:28][OH:29]>CN(C)C=O>[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:25])=[C:14]([C:20]([NH:26][C:27]([CH3:31])([CH3:30])[CH2:28][OH:29])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482668HCID 69482668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-amino-2-methyl-1-propanol employing methods similar to those described in Example 2 and using N,N-dimethylformamide as the reaction solvent. The product was obtained as an off-white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.95 (1H, br s), 10.95 (1H, br s), 10.01 (1H, br s), 8.17 (0.70H, s), 8.13 (0.30H, s), 7.34-7.25 (3H, m), 7.15-7.09 (2H, m), 4.86 (1H, br s), 3.98 (2H, s), 3.50-3.41 (2H, m), 1.29 (3H, s), 1.24 (3H, s); HRMS calcd for C20H20FN3O4+H+: 386.1516. Found 386.1521.

Workup

  1. customThe product was obtained as an off-white solid

Sources & evidence

ORD record
ord-acc59c4e813a48c7b96e367eaf45a911
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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