1-(2-Hydroxyethyl)-4-methylpiperazine → Hydrochloric Acid

HRID 706591Notes

Reaction equation

HRID 706591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH3:33])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28]C=C(C(C)C)[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][OH:43])[CH2:37][CH2:36]1.C[C@H]1[N:50](C)[C@@H:49]([CH3:52])[CH2:48]N(CCO)C1.[ClH:56].CCOCC>CO>[ClH:1].[ClH:56].[CH:49]([N:50]1[CH:28]=[CH:29][C:24]([CH2:23][N:18]2[C:19]3[C:15](=[C:14]([NH:13][C:11]([C:8]4[N:5]5[CH:6]=[CH:7][C:2]([O:43][CH2:42][CH2:41][N:38]6[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]6)=[CH:3][C:4]5=[N:10][CH:9]=4)=[O:12])[CH:22]=[CH:21][CH:20]=3)[C:16]([CH3:33])=[N:17]2)=[N:25]1)([CH3:52])[CH3:48].[ClH:1]

Participants

7

Reactant 4

HCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 10953452Ether hydrochlorideHCID 679740542-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)ethanolHCID 679758637-chloro-N-(1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 2

HCID 313Hydrochloric AcidYield 45%HCID 86699330N-(1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-3-methyl-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide Bis Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to Example 7, Step F, substituting 7-chloro-N-(1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide for 7-chloro-N-(1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide and 2-(4-methylpiperazin-1-yl)ethanol for 2-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)ethanol. The HCl salt was prepared by subjecting the compound to 4M HCl/ether (20 equivalents) in methanol and concentrating under reduced pressure to give the bis-HCl salt (45%). MS (APCI), positive scan, m/z=556.3 (M+H).

Workup

  1. customPrepared
  2. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-598ee1da835646dcb2170ac9db76ee87
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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