Acetic Acid → 6-((cis-2,6-Dimethylmorpholino)methyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 1048893Notes

Reaction equation

HRID 1048893 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=O)=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([NH2:23])=[O:22])=[CH:9]2)=[CH:4][CH:3]=1.[CH3:24][C@H:25]1[O:30][C@@H:29]([CH3:31])[CH2:28][NH:27][CH2:26]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:24][C@H:25]1[CH2:26][N:27]([CH2:18][C:14]2[CH:13]=[C:12]3[C:17](=[CH:16][CH:15]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:9]=[C:10]([C:21]([NH2:23])=[O:22])[C:11]3=[O:20])[CH2:28][C@@H:29]([CH3:31])[O:30]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6415002,6-Dimethylmorpholine, cis-HCID 5049666Sodium triacetoxyborohydrideHCID 1214479581-(4-Fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 1214479166-((cis-2,6-Dimethylmorpholino)methyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamideYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound G (10 mg, 0.032 mmol), cis-2,6-dimethylmorpholine (5 μL, 0.039 mmol), and acetic acid (4.6 μL, 0.081 mmol) in dichloromethane (1 mL) were stirred for one hour. To this mixture was added sodium triacetoxyborohydride (10.2 mg, 0.048 mmol). After 16 hours, the reaction was concentrated to dryness. Purification by reverse phase HPLC afforded 5 mg (38%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.23 (d, J=4.4 Hz, 1H), 8.55 (s, 1H), 8.26 (d, J=1.8 Hz, 1H), 7.77-7.73 (m, 2H), 7.65 (dd, J=8.7, 2 Hz, 1H), 7.59 (d, J=4.4 Hz, 1H), 7.52 (t, J=8.68, 8.76, 2H), 7.03 (d, J=8.68, 1H), 3.57-3.52 (m, 4H), 2.65 (d, J=10.2 Hz, 2H), 1.01 (d, J=6.3 Hz, 6H); ES-MS [M+1]+: 410.3.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-d1d19f86f4da4eb2b4aefd6152dd75c6
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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