Morpholine → HCID 59553161, compound

HRID 1171253Notes

Reaction equation

HRID 1171253 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][N:29]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:10][CH:9]=1)=[O:6].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(O)C>[N:30]1([C:2]2[CH:3]=[C:4]([CH:27]=[CH:28][N:29]=2)[C:5]([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([O:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:10][CH:9]=2)=[O:6])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 59553212HCID 59553212, compound

Product 1

HCID 59553161HCID 59553161, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-isonicotinamide (200 umol, 1 eq), morpholine (2 mmol, 10 eq.) and ethanol (2 ml) is heated at 100° C. for 3-4 days in a 2-dram vial with agitation. The mixture is cooled to room temperature and concentrated. The crude mixture is purified by flash column chromatography and re-crystallized from methanol to afford 2-morpholin-4-yl-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-isonicotinamide. 1H NMR (300 MHz, DMSO-d6) δ 10.41 (s, 1H), 8.31 (d, 1H), 8.21 (m, 1H), 7.85 (m, 1H), 7.58 (m, 2H), 2.42 (m, 2H), 7.23 (d, 1H), 7.08 (d, 1H), 4.38 (t, 2H), 3.78 (m, 4H), 3.60 (m, 8H), 2.88 (t, 2H) 2.58 (m, 4H). MS: 463.3 (M+1).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated
  3. customThe crude mixture is purified by flash column chromatography
  4. customre-crystallized from methanol

Sources & evidence

ORD record
ord-c61a0febb8404b7bb2a04875807fb8c6
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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