Diisopropylethylamine → HCID 11512463, compound

HRID 2116898Notes

Reaction equation

HRID 2116898 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][O:10]COCC[Si](C)(C)C)=[CH:4][N:3]=1.[F:19][C:20]1[CH:21]=[C:22]([C:27]2[N:28]=[C:29]([N:42]3[CH2:47][CH2:46][NH:45][CH2:44][C@H:43]3[CH3:48])[NH:30][C:31]=2[C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[CH:23]=[CH:24][C:25]=1[F:26].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:8][C:7]1[CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=[N:3][C:2]=1[N:45]1[CH2:46][CH2:47][N:42]([C:29]2[NH:30][C:31]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:39])([F:41])[F:40])=[CH:34][CH:33]=3)=[C:27]([C:22]3[CH:23]=[CH:24][C:25]([F:26])=[C:20]([F:19])[CH:21]=3)[N:28]=2)[C@H:43]([CH3:48])[CH2:44]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58625816HCID 58625816, compoundHCID 58625836HCID 58625836, compound

Product 1

HCID 11512463HCID 11512463, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2,3-dichloro-5-(((2-(trimethylsilyl)ethoxy)methoxy)methyl)pyridine from step (a) above (80 mg, 0.26 mmol), (2R)-1-(4-(3,4-difluorophenyl)-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)-2-methylpiperazine (100. mg, 0.236 mmol, Example 1(d)), and DIEA (0.082 mL, 0.47 mmol, Aldrich) in NMP (0.7 mL) was subjected to microwave irradiation at 170° C. for 1 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified on silica gel using ISCO Combiflash® system with EtOAc/Hexanes (1:9) as the eluant to give the title compound as a light brown solid. MS (ESI, positive ion) m/z: 694 (M+1).

Workup

  1. customirradiation at 170° C. for 1 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified on silica gel using ISCO Combiflash® system with EtOAc/Hexanes (1:9) as the eluant

Sources & evidence

ORD record
ord-ed458610b8544077badf4d80d1049c64
Source dataset
uspto-grants-2008_10
Patent number
US07439360B2

Reaction notes

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