p-Toluenesulfonic acid → 3-Methoxypropyl-6-[(tetrahydro-2H-pyran-2-yloxy)carbamoyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2036893Notes

Reaction equation

HRID 2036893 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][OH:6].[C:7]([N:14]1[CH:18]=[CH:17]N=[CH:15]1)(N1C=CN=C1)=[O:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:36][NH:37][C:38]([C:40]1[CH:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)CNCC2)=[O:39]>ClCCl.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([N:14]1[CH2:15][CH2:47][C:48]2[C:17](=[CH:42][CH:41]=[C:40]([C:38](=[O:39])[NH:37][O:36][CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][O:30]3)[CH:49]=2)[CH2:18]1)=[O:8]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 682631,1'-CarbonyldiimidazoleHCID 741163-Methoxy-1-propanolHCID 86656618HCID 86656618, compound

Product 1

HCID 866565953-Methoxypropyl-6-[(tetrahydro-2H-pyran-2-yloxy)carbamoyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.069 ml 3-methoxypropanol in 4 ml dichloromethane are treated with 117 mg carbonyldiimidazole and 10 mg p-toluenesulfonic acid. After 2 h at ambient temperature, 200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide are added and the reaction mixture is stirred overnight at ambient temperature. Subsequently, the mixture is treated with 2 ml of water and the organic phase is separated. The aqueous phase is extracted twice with 5 ml dichloromethane, dried and evaporated. 100 mg of colorless oil are obtained.

Workup

  1. customthe organic phase is separated
  2. extractionThe aqueous phase is extracted twice with 5 ml dichloromethane
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-bc2e302aa22447bb832699863b29c772
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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