Water → N2-(3-methoxypropyl)-N6-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,6(1H)-dicarboxamide

HRID 2036892Notes

Reaction equation

HRID 2036892 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7]([N:14]1[CH:18]=[CH:17]N=[CH:15]1)(N1C=CN=C1)=[O:8].[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][NH:26][C:27]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)CNCC2)=[O:28].O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([N:14]1[CH2:15][CH2:36][C:37]2[C:17](=[CH:31][CH:30]=[C:29]([C:27]([NH:26][O:25][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][O:19]3)=[O:28])[CH:38]=2)[CH2:18]1)=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 16723-MethoxypropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 86656618HCID 86656618, compound

Product 1

HCID 86656594N2-(3-methoxypropyl)-N6-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,6(1H)-dicarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.074 ml 3-methoxyproylamine in 4 ml DMF is treated under an inert gas atmosphere is treated with 117 mg carbonyldiimidazole. After 2 h at ambient temperature the resulting mixture is treated with 200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide and 10 mg DMAP. The reaction mixture is stirred overnight. After addition of 2 ml water the mixture is extracted twice with dichloromethane and the combined organic phases are dried and evaporated. The residue is purified by silica gel flash chromatography. 180 mg of yellowish oil are obtained.

Workup

  1. additionis treated under an inert gas atmosphere
  2. extractionis extracted twice with dichloromethane
  3. customthe combined organic phases are dried
  4. customevaporated
  5. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-68725e10fd44477f8b2b417d462a8f1b
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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