Methoxyisopropylamine → HCID 69480934, compound

HRID 2364232Notes

Reaction equation

HRID 2364232 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](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[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](=[O:27])[N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 123458MethoxyisopropylamineHCID 69480365HCID 69480365, compound

Product 1

HCID 69480934HCID 69480934, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-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 10.07 (1H, d, J=8 Hz), 8.55 (1H, s), 7.16 (2H, dd, J=9, 6 Hz), 7.03 (2H, t, J=9 Hz), 6.93 (1H, s), 4.97 (1H, d, J=17 Hz), 4.90 (1H, d, J=17 Hz), 4.34 (1H, m), 4.11 (2H, s), 3.50 (2H, m), 3.44 (4H, m), 3.38 (3H, s), 1.69 (2H, m), 1.57 (2H, m), 1.52 (2H, m), 1.28 (3H, d, J=7 Hz); HRMS calcd for C27H31FN4O5+H+: 511.2357. Found: 511.2162.

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-ef437e08fcd548fc97856ea4040031f2
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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