Methoxyisopropylamine → HCID 69481031, compound

HRID 2364242Notes

Reaction equation

HRID 2364242 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:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:35][O:36][CH2:37][CH:38]([NH2:40])[CH3:39]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:34])=[C:14]([C:29]([NH:40][CH:38]([CH3:39])[CH2:37][O:36][CH3:35])=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)=[O:21])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 123458MethoxyisopropylamineHCID 58882959HCID 58882959, compound

Product 1

HCID 69481031HCID 69481031, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(4-morpholinyl)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (±)-1-(methyloxy)-2-propanamine employing methods similar to those those described in Example 9 and was purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as an off-white rigid foam: 1H NMR (CDCl3) δ 10.01 (1H, d, J=8 Hz), 8.57 (1H, s), 7.15 (2H, dd, J=8.6, 5.5 Hz), 7.03 (3H, m), 4.98 (1H, d, J=17 Hz), 4.91 (1H, d, J=17 Hz), 4.34 (1H, m), 4.12 (2H, s), 3.73 (2H, m), 3.68 (2H, m), 3.56 (4H, m), 3.45 (2H, d, J=5 Hz), 3.39 (3H, s), 1.29 (3H, d, J=7 Hz); HRMS calcd for C26H29FN4O6+H+: 513.2149. Found: 513.2145.

Workup

  1. customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
  2. customThe product was obtained as an off-white rigid foam

Sources & evidence

ORD record
ord-ca4c338257fb41d091189872a2e261b5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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