3-Methoxypropylamine → HCID 69482157, compound

HRID 2364561Notes

Reaction equation

HRID 2364561 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](OCC)=[O:32])[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][O:38][CH2:39][CH2:40][CH2:41][NH2:42]>>[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:42][CH2:41][CH2:40][CH2:39][O:38][CH3:37])=[O:32])[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

3

Reactant 2

HCID 16723-MethoxypropylamineHCID 69481817HCID 69481817, compound

Product 1

HCID 69482157HCID 69482157, compound

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 [3-(methyloxy)propyl]amine using methods similar to Example 563 to provide an orange solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.54 (d, J=3.58 Hz, 4 H), 1.64 (d, J=7.16 Hz, 2 H), 1.69-1.75 (m, 2 H), 1.77-1.82 (m, 2 H), 2.38-2.44 (m, 2 H), 3.24-3.26 (m, 3 H), 3.34-3.47 (m, 8 H), 4.15-4.25 (m, 4 H), 7.11-7.18 (m, 2 H), 7.40 (dd, J=8.63, 5.69 Hz, 2 H), 8.00 (s, 1 H), 8.56 (d, J=1.26 Hz, 1 H), 10.34 (t, J=5.90 Hz, 1 H), 17.19 (s, 1 H); ES+ MS: 539 (M+H+).

Workup

  1. customto provide an orange solid

Sources & evidence

ORD record
ord-30cc03e24cf54b70b554bc89c70b2bf6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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