Piperazine → HCID 136206991, compound

HRID 339305Notes

Reaction equation

HRID 339305 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7](=[O:17])[NH:8][C:9]([CH2:15]Cl)=[N:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[NH:24]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7](=[O:17])[NH:8][C:9]([CH2:15][N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4].[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7](=[O:17])[NH:8][C:9]([CH2:15][N:24]3[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4]

Participants

6

Reactant 3

HCID 4837PiperazineHCID 68163Hexahydro-1,4-diazepineHCID 136206988HCID 136206988, compound

Product 2

HCID 136206991HCID 136206991, compoundHCID 136342878HCID 136342878, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Displacement of the chloro group of compound 4 with piperazine or [1,4]diazepane using General procedure F provides the compound 47A or 47B. To a stirring solution of 4 (1 eq) in acetonitrile was added piperazine or [1,4]diazepane (large excess) under a blanket of nitrogen. The solution was allowed to stir overnight and then evaporated to dryness. The crude material was purified via silica plug with 9:1 dichloromethane:methanol to afford a white solid, 4-Oxo-2-piperazin-1-ylmethyl-3,4-dihydro-quinazoline-5-carboxylic acid methyl ester, 47A or 2-[1,4]diazepan-1-ylmethyl-4-oxo-3,4-dihydro-quinazoline-5-carboxylic acid methyl ester, 47B.

Workup

  1. customevaporated to dryness
  2. customThe crude material was purified via silica plug with 9:1 dichloromethane

Sources & evidence

ORD record
ord-7d5ef44dbcef4b7b9fac999a01907ad0
Source dataset
uspto-grants-2014_11
Patent number
US08894989B2

Reaction notes

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