Triethylamine → HCID 69480298, compound

HRID 2364471Notes

Reaction equation

HRID 2364471 reaction equation
F[P-](F)(F)(F)(F)F.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([OH:38])=[C:21]([C:31]([NH:33][CH2:34][CH2:35][O:36][CH3:37])=[O:32])[C:22](=[O:30])[N:23]3[CH2:26][C:27]([OH:29])=O)=[N:18][CH:17]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C.[CH:46]1([NH2:50])[CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[CH:46]1([NH:50][C:27](=[O:29])[CH2:26][N:23]2[C:24]3[C:19](=[N:18][CH:17]=[C:16]([CH2:15][C:12]4[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=4)[CH:25]=3)[C:20]([OH:38])=[C:21]([C:31]([NH:33][CH2:34][CH2:35][O:36][CH3:37])=[O:32])[C:22]2=[O:30])[CH2:49][CH2:48][CH2:47]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886HexafluorophosphateHCID 75645CyclobutylamineHCID 59776534[7-[(4-fluorophenyl)methyl]-4-hydroxy-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetic acid

Product 1

HCID 69480298HCID 69480298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluroniuum hexafluorophosphate (57 mg, 0.15 mmol) was added to a mixture of [7-[(4-fluorophenyl)methyl]-4-hydroxy-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,5-naphthyridine-1(2H)-yl]acetic acid, the title compound in Example 171 (50 mg, 0.12 mmol), triethylamine (0.02 mL, 0.15 mmol) and cyclobutylamine (0.012 mL, 0.15 mmol) in DMF (1 mL) at rt. After 1 h, the mixture was diluted with H2O (4 mL) and the title compound was collected by filtration to give a white solid: 1H NMR (d6-DMSO) δ 10.22 (1H, m), 8.54 (1H, s), 8.42 (1H, m), 7.75 (1H, s), 7.31 (2H, m), 7.10 (2H, m), 4.81 (2H, s), 4.13 (1H, m), 4.10 (2H, s), 3.52 (4H, m), 3.27 (3H, s), 2.09 (2H, m), 1.84 (2H, m), 1.59 (2H, m); HRMS calcd for C25H27FN4O5+H+: 483.2044. Found: 483.2049.

Sources & evidence

ORD record
ord-79436d0adfc241bcb208a332fcd1a875
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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