Methylamine → HCID 69482770, compound

HRID 2364566Notes

Reaction equation

HRID 2364566 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:36])=[C:14]([C:31]([O:33]CC)=O)[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:37][NH2:38]>C(O)C>[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:36])=[C:14]([C:31]([NH:38][CH3:37])=[O:33])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 69481817HCID 69481817, compound

Product 1

HCID 69482770HCID 69482770, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and N-methylamine in ethanol using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.54 (d, J=4.42 Hz, 4 H), 1.61-1.77 (m, 4 H), 2.35-2.44 (m, 2 H), 2.91 (d, J=4.84 Hz, 3 H), 3.34-3.42 (m, 4 H), 4.14-4.23 (m, 4 H), 7.14 (t, J=8.95 Hz, 2 H), 7.40 (dd, J=8.84, 5.48 Hz, 2 H), 7.99 (s, 1 H), 8.56 (d, J=1.47 Hz, 1 H), 10.14 (d, J=4.63 Hz, 1 H), 17.22 (s, 1 H); ES+ MS: 481 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-13d73fe2d4aa4897a20b55ad2405487f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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