N-methyl-2-pyrrolidone → HCID 86709409, compound

HRID 2172276Notes

Reaction equation

HRID 2172276 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C@H:8]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=1)[O:7]2)([O-:3])=[O:2].CN1CCCC1=O.Cl[CH:35]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=2)=[CH:39][CH:38]=1)[CH3:36].C(N(C(C)C)CC)(C)C>O>[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C@H:8]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24]([CH:35]([C:37]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][C:48]([C:51]([F:52])([F:53])[F:54])=[CH:47][CH:46]=5)=[CH:39][CH:38]=4)[CH3:36])[CH2:23][CH2:22]3)=[CH:17][CH:16]=1)[O:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 70874384HCID 70874384, compoundHCID 86709410HCID 86709410, compound

Product 1

HCID 86709409HCID 86709409, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-2-Nitro-7-(4-piperazin-1-ylphenoxymethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (0.56 g) was added to an N-methylpyrrolidone solution (5 ml) of 1-(1-chloroethyl)-4-(4-trifluoromethylbenzyloxy)benzene (0.54 g). Subsequently, diisopropylethylamine (0.54 ml) was added thereto, and the mixture was stirred at room temperature for 12 hours. Thereafter, the mixture was heated to 60° C. and stirred for 7 hours. Water was added to the reaction mixture and the precipitated solid was collected by filtration. The solid thus obtained was purified by basic silica gel column chromatography (methylene chloride) and recrystallized from acetone-water to afford the title compound as a slightly yellow powder (0.15 g).

Workup

  1. temperatureThereafter, the mixture was heated to 60° C.
  2. stirringstirred for 7 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. customThe solid thus obtained
  5. customwas purified by basic silica gel column chromatography (methylene chloride)
  6. customrecrystallized from acetone-water

Sources & evidence

ORD record
ord-ee97c4f25bdb4e20b77339a5242d1296
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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