1-(2-Hydroxyethyl)-4-methylpiperazine → HCID 136352235, compound

HRID 1853287Notes

Reaction equation

HRID 1853287 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)=[CH:14][CH:15]=2)[O:10][C:9]([C:26]2[N:27]=[CH:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:8]1)(C)(C)C.[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44]O)[CH2:39][CH2:38]1>>[CH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[C:26]([C:9]2[O:10][C:11]3[C:16]([C:7](=[N:6][OH:5])[CH:8]=2)=[CH:15][CH:14]=[C:13]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:44][CH2:43][N:40]4[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]4)[CH:20]=2)[CH:12]=3)[N:27]=1

Participants

3

Reactant 2

HCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 86673056HCID 86673056, compound

Product 1

HCID 136352235HCID 136352235, compound

Procedure

2-Isoquinolin-3-yl-7-{3-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenylethynyl}-chromen-4-one oxime was prepared in 9% overall yield using the method described in examples 44 and 44A, starting from 7-(3-hydroxyphenyl)ethynyl-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (tert-butyl protected oxime of example 30) and 2-(4-methyl-piperazin-1-yl)-ethanol. The title compound was isolated as a yellow solid and as a 90/10 mixture of Z/E oxime isomers after Preparative HPLC purification (gradient 65-50% Water/acetonitrile+0.05% trifluoroacetic acid).

Workup

  1. customoverall yield

Sources & evidence

ORD record
ord-36344ef985ee4c1996d8924fd4ae19a1
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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