Hydrochloric Acid → (R)-2-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one

HRID 1179650Notes

Reaction equation

HRID 1179650 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([NH:26][CH2:27][CH:28]4[CH2:32][CH2:31][CH2:30][N:29]4[C:33]([O:35]C(C)(C)C)=O)[CH:23]=[CH:24][CH:25]=3)[CH2:14][CH2:13]2)[N:3]=1.Cl.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(NC(C)C)(C)C>CO.CCOCC>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([N:26]4[CH2:27][C@H:28]5[CH2:32][CH2:31][CH2:30][N:29]5[C:33]4=[O:35])[CH:23]=[CH:24][CH:25]=3)[CH2:16][CH2:17]2)[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 94429TriphosgeneHCID 765409851,1-Dimethylethyl 2-{[(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)amino]methyl}-1-pyrrolidinecarboxylate

Product 1

HCID 57463854(R)-2-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (R)-(1,1-dimethylethyl 2-{[(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)amino]methyl}-1-pyrrolidinecarboxylate in methanol was treated with absolution of hydrogen chloride in ether (1 M). The resulting mixture was stirred 30 minutes then concentrated under vacuum and then loaded onto an ion-exchange cartridge (SCX-2) and eluted with methanol followed by ammonia in methanol (1 M). The combined basic fractions were concentrated under vacuum. The residue, (10 mg) was then dissolved in DCM (1 mL) and treated with triphosgene (23 mg, 0.3 eq.), diisopropylamine (4 uL, 3 eq.). The mixture was stirred for 1 h then concentrated under vacuum and purified by preparative mass-directed hplc to afford the title compound (3.1 mg).

Workup

  1. concentrationthen concentrated under vacuum
  2. washeluted with methanol
  3. concentrationThe combined basic fractions were concentrated under vacuum
  4. dissolutionThe residue, (10 mg) was then dissolved in DCM (1 mL)
  5. stirringThe mixture was stirred for 1 h
  6. concentrationthen concentrated under vacuum
  7. custompurified by preparative mass-directed hplc

Sources & evidence

ORD record
ord-70374935b26747dcb98fdeb325041d6d
Source dataset
uspto-grants-2007_10
Patent number
US07279481B2

Reaction notes

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