N,N-Dimethylpropargylamine → HCID 136352229, compound

HRID 1853275Notes

Reaction equation

HRID 1853275 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)(C)(C)C.[CH3:28][N:29]([CH2:31][C:32]#[CH:33])[CH3:30]>>[CH3:28][N:29]([CH3:30])[CH2:31][C:32]#[C:33][C:13]1[CH:12]=[C:11]2[C:16]([C:7](=[N:6][OH:5])[CH:8]=[C:9]([C:18]3[N:19]=[CH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:10]2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 86673023HCID 86673023, compound

Product 1

HCID 136352229HCID 136352229, compound

Procedure

7-(3-dimethylamino-prop-1-ynyl)-2-isoquinolin-3-yl-chromen-4-one oxime was prepared in 20% overall yield using the method described in example 24, starting from 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (example 2B) and N,N-dimethylamino-2-propyne. The title compound was purified by preparative HPLC (gradient 70-55% Water/acetonitrile+0.05% trifluoroacetic acid) and isolated as an orange solid and as a 85/15 mixture of Z/E oxime isomers.

Workup

  1. customoverall yield
  2. customThe title compound was purified by preparative HPLC (gradient 70-55% Water/acetonitrile+0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-a81354a04ed7424c89d90bccb08014b4
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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