Isopropanol → HCID 67265107, compound

HRID 1685203Notes

Reaction equation

HRID 1685203 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].Cl[C:29]1[C:30]2[C:37](=[CH:38][C:39]3[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=3)[C:36](=[O:45])[NH:35][C:31]=2[N:32]=[CH:33][N:34]=1.CCN(C(C)C)C(C)C.CC(O)C>O>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:22]3[CH2:23][CH2:24][N:25]([C:29]4[C:30]5[C:37](=[CH:38][C:39]6[CH:40]=[CH:41][N:42]=[CH:43][CH:44]=6)[C:36](=[O:45])[NH:35][C:31]=5[N:32]=[CH:33][N:34]=4)[CH2:26][CH2:27]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]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 67264736HCID 67264736, compoundHCID 86641619HCID 86641619, compound

Product 1

HCID 67265107HCID 67265107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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); 4-chloro-5-[1-pyridin-4-yl-methylidene]-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.34 g; 0.0013 mol; 1.0 equiv); DIPEA (1.7 mL; 0.0098 mol; 7.6 equiv); 2-propanol (15 mL) and microwave at 80° C. for 20 min. Cool and dilute with water. Extract with EA and wash with brine. Concentrate the crude and purify by reverse phase HPLC to give the title compound as a mixture of E and Z isomers (0.04 g; 5.4%). MS (ES+): m/z=573 (M+H). (Note: All olefin compounds are mixtures of E and Z isomers.)

Workup

  1. temperatureCool
  2. extractionExtract with EA
  3. washwash with brine
  4. concentrationConcentrate the crude
  5. custompurify by reverse phase HPLC

Sources & evidence

ORD record
ord-defb5f777d274bfda55eec83fcdc69fd
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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