Diisopropylethylamine → HCID 67265578, compound

HRID 1685175Notes

Reaction equation

HRID 1685175 reaction equation
Cl.Cl.Cl.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11].[CH:28](=[C:35]1[C:43]2[C:42](Cl)=[N:41][CH:40]=[N:39][C:38]=2[NH:37][C:36]1=[O:45])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH:28](=[C:35]1[C:43]2[C:42]([N:25]3[CH2:24][CH2:23][CH:22]([C:14]4[N:15]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH:16]=[C:12]([C:7]5[CH:8]=[CH:9][C:10]([F:11])=[C:5]([Cl:4])[CH:6]=5)[N:13]=4)[CH2:27][CH2:26]3)=[N:41][CH:40]=[N:39][C:38]=2[NH:37][C:36]1=[O:45])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67264736HCID 67264736, compoundHCID 86641606HCID 86641606, compound

Product 1

HCID 67265578HCID 67265578, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combine {2-[4-(3-chloro-4-fluoro-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-ethyl}-dimethyl-amine tris hydrochloride (0.5 g; 0.0013 mol; 1.0 equiv); 5-benzylidene-4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.33 g; 0.0013 mol; 1.0 equiv); DIPEA (1.7 mL 0.0098 mol; 7.6 equiv); 2-propanol (10 mL) and microwave at 100° C. for 30 min. Cool and concentrate in vacuo. Dilute with saturated sodium bicarbonate solution and extract with DCM. Wash organic layer with water and brine and dry over anhydrous sodium sulfate. Concentrate the crude compound and purify by reverse phase HPLC to give the title compound as a mixture of E and Z isomers (0.09 g; 12.2%). MS (ES+): m/z=572 (M+H)

Workup

  1. temperatureCool
  2. concentrationconcentrate in vacuo
  3. additionDilute with saturated sodium bicarbonate solution
  4. extractionextract with DCM
  5. dry with materialWash organic layer with water and brine and dry over anhydrous sodium sulfate
  6. concentrationConcentrate the crude compound
  7. custompurify by reverse phase HPLC

Sources & evidence

ORD record
ord-eb0fea665a15427b8dfa662106b8a4b0
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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