Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86301334, compound

HRID 1748388Notes

Reaction equation

HRID 1748388 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18](N(OC)C)=[O:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.F[C:27]1C=CC(COC2C=C3C(C=C(C(Cl)=O)C=N3)=CC=2)=CC=1.Cl.CNOC.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18](=[O:19])[CH3:27])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 90417201HCID 90417201, compoundHCID 90417207HCID 90417207, compound

Product 1

HCID 86301334HCID 86301334, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-((4-Fluorobenzyl)oxy)-N-methoxy-N-methylquinoline-3-carboxamide. To a solution of 7-((4-fluorobenzyl)oxy)quinoline-3-carbonyl chloride in DCM (14 mL) was added N,O-dimethylhydroxylamine hydrochloride (207 mg, 2.12 mmol) and DIPEA (0.739 mL, 4.23 mmol). The reaction was stirred for 15 minutes at ambient temperature before being concentrated onto silica. Purification (FCC, SiO2, 0-80%, EtOAc/hexanes) afforded the title compound as a white solid (324 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 9.18 (d, J=2.0 Hz, 1H), 8.54 (d, J=1.6 Hz, 1H), 7.81 (d, J=9.0 Hz, 1H), 7.52 (d, J=2.0 Hz, 1H), 7.51-7.44 (m, 2H), 7.32 (dd, J=2.3, 9.0 Hz, 1H), 7.11 (t, J=8.8 Hz, 2H), 5.21 (s, 2H), 3.59 (s, 3H), 3.45 (d, J=0.8 Hz, 3H). [M+H]=341.3.

Workup

  1. concentrationbefore being concentrated onto silica
  2. customPurification (FCC, SiO2, 0-80%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-0533eb76833044f7b34727aedf3e432b
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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