Water → HCID 72303593, compound

HRID 1747094Notes

Reaction equation

HRID 1747094 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH:18]([C:19]([NH:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][OH:31])[N:25]=2)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:32])[N:10]1[CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[NH:39][S:40]([CH3:43])(=[O:42])=[O:41].N1[CH:49]=[CH:48]C=CC=1.[C:50](OC(=O)C)(=[O:52])[CH3:51].[OH2:57]>ClCCl.CN(C1C=CN=CC=1)C>[C:50]([O:31][CH2:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][O:22][N:21]([C:48](=[O:57])[CH3:49])[C:19]([CH:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:32])[N:10]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]3[NH:39][S:40]([CH3:43])(=[O:41])=[O:42])[CH:9]2[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[O:20])[N:25]=1)(=[O:52])[CH3:51]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 72303700HCID 72303700, compound

Product 1

HCID 72303593HCID 72303593, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 480 mg of (3RS,4RS)-3-(2,4-dichlorophenyl)-N-{[6-(hydroxymethyl)pyridin-2-yl]methoxy}-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide in 4.8 ml of dichloromethane was cooled to 0° C., 4.5 mg of DMAP and 0.13 ml of pyridine were added, and then 0.7 ml of acetic anhydride was added dropwise, followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:chloroform-methanol) to obtain (6-{[(acetyl {[3-(2,4-dichlorophenyl)-2-{2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)oxy]methyl}pyridin-2-yl)methyl acetate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent:chloroform-methanol)

Sources & evidence

ORD record
ord-97ceec013bc449199c8576e64756268a
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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