Water → HCID 68875035, compound

HRID 1435969Notes

Reaction equation

HRID 1435969 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13]S(C)(=O)=O)[CH2:9]1)=O)(C)(C)C.[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][C:25](O)=[CH:26][CH:27]=2)[CH:22]=[CH:21][N:20]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O.CO.C(O)(=O)C>[NH:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:25]2[CH:24]=[C:23]3[C:28](=[CH:27][CH:26]=2)[C:19]([NH2:18])=[N:20][CH:21]=[CH:22]3)[CH2:9]1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylateHCID 1357539911-Aminoisoquinolin-6-ol

Product 1

HCID 68875035HCID 68875035, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (R)-3-methanesulfonyloxypyrrolidine-1-carboxylic acid tert-butyl ester (2.95 g) in N, N-dimethylformamide (2 ml) was added dropwise to a stirred solution of 1-amino-6-hydroxyisoquinoline (1.2 g, 7.4 mmol) and K2CO3 (1.02 g, 7.4 mmol) in N, N-dimethylformamide (10 ml) at 100° C. The mixture was stirred for 1 h then cooled and water added. The mixture was acidified with glacial acetic acid then diluted with methanol. The mixture was loaded onto a pre-acidified SCX column using methanol and eluted with 2M ammonia in methanol to afford crude (S)-6-(pyrrolidin-3-yloxy)isoquinolin-1-ylamine, which was purified by flash chromatography on silica (eluent: 10% methanol in DCM with 1% ammonium hydroxide), El-MS: m/z=230.3 [M+H]+.

Workup

  1. temperaturethen cooled
  2. washeluted with 2M ammonia in methanol

Sources & evidence

ORD record
ord-bac9ee17dc974226b47dd21b24acbc56
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

Loading…