1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59322396, compound

HRID 1685205Notes

Reaction equation

HRID 1685205 reaction equation
Cl.Cl.Cl.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:15]([CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11].Cl[C:31]1[C:32]2[C:39]([CH3:41])([CH3:40])[C:38](=[O:42])[NH:37][C:33]=2[N:34]=[CH:35][N:36]=1.N12CCCN=C1CCCCC2>CC(O)C>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:24]3[CH2:25][CH2:26][N:27]([C:31]4[C:32]5[C:39]([CH3:40])([CH3:41])[C:38](=[O:42])[NH:37][C:33]=5[N:34]=[CH:35][N:36]=4)[CH2:28][CH2:29]3)[N:15]([CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67265197HCID 67265197, compoundHCID 86641620HCID 86641620, compound

Product 1

HCID 59322396HCID 59322396, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combine 4-[4-(3-Chloro-4-fluoro-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-1H-imidazol-2-yl]-piperidine tris hydrochloride (0.3 g; 0.00062 mol), 4-chloro-5,5-dimethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.16 g; 0.0008 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.76 mL; 0.0051 mol) into IPA (10 mL) and stir at 120° C. for 16 h; cool and concentrate. Quench the reaction with saturated sodium bicarbonate solution and extract with EA. Evaporate the EA layer and purify by column chromatography using 0-5% MeOH/DCM as eluent to afford the title compound (0.045 g; 13.5%). MS (ES+): m/z=538 (M+1).

Workup

  1. temperaturecool
  2. concentrationconcentrate
  3. customQuench
  4. customthe reaction with saturated sodium bicarbonate solution
  5. extractionextract with EA
  6. customEvaporate the EA layer
  7. custompurify by column chromatography

Sources & evidence

ORD record
ord-a9989efe2b80445c808738b186a31316
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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