N-methyl-2-pyrrolidone → HCID 60045645, compound

HRID 1064583Notes

Reaction equation

HRID 1064583 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4]N=1.[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([N:22]2[CH:27]([CH3:28])[CH2:26][N:25]([C:29](O)=O)[CH2:24][CH:23]2[CH3:32])=[N:14][CH:13]=1.CC1NC(C)CN([C:41]([O-])=[O:42])C1.C([N:47]([CH2:51][CH3:52])[CH:48]([CH3:50])C)(C)C.CN1CCCC1=[O:59]>>[CH3:28][C@H:27]1[N:22]([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=[CH:13][N:14]=2)[C@@H:23]([CH3:32])[CH2:24][N:25]([CH2:29][C:4]([NH:5][C:6]2[CH:7]=[C:8]([O:42][CH:41]3[CH2:50][CH2:48][NH:47][CH2:51][CH2:52]3)[CH:9]=[CH:10][C:11]=2[CH3:2])=[O:59])[CH2:26]1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 22273362HCID 22273362, compoundHCID 22273418HCID 22273418, compound

Product 1

HCID 60045645HCID 60045645, compound

Procedure

1,1-Dimethylethyl, 4-(4-quinazolinyl)-3,5-dimethylpiperazine-1-carboxylate 4-Chloroquinazoline (6 g), cis-1,1-diethylethyl, 3,5-dimethylpiperazine-1-carboxylate (7.8 g), N,N-diisopropylethylamine (32 ml) in 1-methyl-2-pyrrolidinone (70 ml) were heated at 120° C. for 6 days under nitrogen. The mixture was partitioned between ethyl acetate and brine. The organic phase collected and further washed with brine (×2), collected, dried (MgSO4) and solvent evaporated under reduced pressure to leave a pale brown solid. Purification was by silica gel chromatograpy eluting with ethyl acetate/iso-hexane (3:7) to give the subtitle compound as a pale yellow oil. Yield: 1.1 g

Workup

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. customThe organic phase collected
  3. washfurther washed with brine (×2)
  4. customcollected
  5. dry with materialdried (MgSO4) and solvent
  6. customevaporated under reduced pressure
  7. customto leave a pale brown solid
  8. customPurification
  9. washeluting with ethyl acetate/iso-hexane (3:7)

Sources & evidence

ORD record
ord-a400d6f183ce473391475dadd88e6a2a
Source dataset
uspto-grants-2005_11
Patent number
US06969713B2

Reaction notes

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