1-Isopropylpiperazine → HCID 178456369, compound

HRID 2116901Notes

Reaction equation

HRID 2116901 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13](COCC[Si](C)(C)C)[C:12]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:24][CH2:23]3)=[N:11][C:10]=2[C:38](O)=[O:39])=[CH:5][CH:4]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[CH:79]([N:82]1[CH2:87][CH2:86][NH:85][CH2:84][CH2:83]1)([CH3:81])[CH3:80]>C(Cl)Cl>[CH:79]([N:82]1[CH2:87][CH2:86][N:85]([C:38]([C:10]2[N:11]=[C:12]([N:22]3[CH2:23][CH2:24][N:25]([C:28]4[C:33]([C:34]([F:37])([F:35])[F:36])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:26][CH2:27]3)[NH:13][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:41])([F:42])[F:1])=[CH:4][CH:5]=2)=[O:39])[CH2:84][CH2:83]1)([CH3:81])[CH3:80]

Participants

6

Reactant 4

HCID 780131-IsopropylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58625820HCID 58625820, compound

Product 1

HCID 178456369HCID 178456369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(4-(trifluoromethyl)phenyl)-2-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid from step (e) above (200. mg, 0.325 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (216 mg, 0.488 mmol, Aldrich), DIEA (0.17 mL, 0.98 mmol, Aldrich), and 1-isopropylpiperazine (62 mg, 0.49 mmol, Aldrich) in DCM (2 mL) was stirred at RT for 70 h. The solvents were removed and the residue was purified on silica gel using ISCO Combiflash® system with DCM/2M methanolic ammonia gradient to give the title compound, which was used in the next step. MS (ESI, positive ion) m/z: 726 (M+1).

Workup

  1. customThe solvents were removed
  2. customthe residue was purified on silica gel using ISCO Combiflash® system with DCM/2M methanolic ammonia gradient

Sources & evidence

ORD record
ord-d7791d0bc86a42b69b75dd1fad8ce496
Source dataset
uspto-grants-2008_10
Patent number
US07439360B2

Reaction notes

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