1,2-Dichloroethane → HCID 58345391, compound

HRID 1877992Notes

Reaction equation

HRID 1877992 reaction equation
O=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH:17]([OH:19])=O.[Cl:20][C:21]1[CH:22]=[C:23]([N:27]2[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([S:38][C:39]([F:42])([F:41])[F:40])[CH:33]=3)=[CH:30][C:29]([C:43]([N:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)=[O:44])=[N:28]2)[CH:24]=[CH:25][CH:26]=1.ClC1C=C(N2C(C3C=CC=C(SC(F)(F)F)C=3)=CC(C(O)=O)=N2)C=CC=1.N1CCNCC1>CN(C=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([N:27]2[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([S:38][C:39]([F:41])([F:42])[F:40])[CH:33]=3)=[CH:30][C:29]([C:43]([N:45]3[CH2:50][CH2:49][N:48]([CH:17]=[O:19])[CH2:47][CH2:46]3)=[O:44])=[N:28]2)[CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 7

HCID 111,2-DichloroethaneHCID 284Formic AcidHCID 977OxygenHCID 4837PiperazineHCID 757711-HydroxybenzotriazoleHCID 58345430HCID 58345430, compoundHCID 67312911HCID 67312911, compound

Product 1

HCID 58345391HCID 58345391, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under exclusion of oxygen, 17.2 mg (0.09 mmol) of EDC and 11.7 mg (0.09 mmol) of HOBt and 8.3 mg (0.18 mmol) of formic acid are added to a solution of 35.0 mg (0.07 mmol) of 1-{[1-(3-chlorophenyl)-5-(3-trifluoromethylthiophenyl)-1H-pyrazol-3-yl]carbonyl}piperazine, prepared from the compound of example 8A and piperazine in analogy to example 1, in 1 ml DMF, and the mixture is stirred for 72 hours at room temperature. The reaction mixture is separated by preparative HPLC. 15.7 mg (42% yield of theory) of product are obtained.

Workup

  1. customThe reaction mixture is separated by preparative HPLC
  2. custom15.7 mg (42% yield of theory) of product are obtained

Sources & evidence

ORD record
ord-0daee40b48be43d1a6f1c3eb62ca51c0
Source dataset
uspto-grants-2012_11
Patent number
US08314089B2

Reaction notes

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