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Ethyl Acetate → HCID 18399146, compound

HRID 1019371
Notes
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Reaction equation

HRID 1019371 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[C:7]([C:19]([O:21][CH3:22])=[O:20])[N:8]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:9]2=[O:12])=[CH:4][C:3]=1[O:35][CH3:36].Cl.[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH2:44][Cl:45].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[ClH:45].[CH3:36][O:35][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH2:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][N:38]=1)[C:9](=[O:12])[N:8]([N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)[C:7]([C:19]([O:21][CH3:22])=[O:20])=[C:6]2[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 18399215HCID 18399215, compound

Product 1

HCID 18399146HCID 18399146, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound obtained in Example 2 (300 mg) in dimethylformamide (3 ml) are added 2-picolyl chloride hydrochloride (118 mg) and potassium carbonate (182 mg), and the mixture is stirred at 50° C. overnight. To the mixture are added ethyl acetate and water. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue (chemical name; 6-methoxy-3-methoxycarbonyl-2-morpholino-7-(2-pyridylmethyloxy)-4-(3,4,5-trimethoxyphenyl-1(2H)-isoquinolinone) is dissolved in ethyl acetate, and thereto is added a 4M solution of hydrogen chloride in ethyl acetate (150 μl). The mixture is stirred at room temperature for 30 minutes. The precipitated crystals are collected by filtration, and washed with ethyl acetate to give 6-methoxy-3-methoxycarbonyl-2-morpholino-7-(2-pyridylmethyloxy)-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone hydrochloride (279 mg) as listed in Table 1.

Workup

  1. customThe ethyl acetate layer is separated
  2. washwashed
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. dissolution6-methoxy-3-methoxycarbonyl-2-morpholino-7-(2-pyridylmethyloxy)-4-(3,4,5-trimethoxyphenyl-1(2H)-isoquinolinone) is dissolved in ethyl acetate
  6. additionis added a 4M solution of hydrogen chloride in ethyl acetate (150 μl)
  7. stirringThe mixture is stirred at room temperature for 30 minutes
  8. filtrationThe precipitated crystals are collected by filtration
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-6037f1167e2142f39ac0fd73753f3b0d
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06486155B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes