Diisopropylethylamine → HCID 178442204, compound

HRID 2113504Notes

Reaction equation

HRID 2113504 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[NH:11][N:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]=1[CH2:17][CH2:18][NH2:19].C(N(C(C)C)CC)(C)C.[CH2:29]([C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1)[CH2:30][CH2:31][CH2:32][CH3:33]>ClCCl>[CH2:29]([C:34]1[CH:35]=[CH:36][C:37]([S:40]([NH:19][CH2:18][CH2:17][C:8]2[C:9]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)=[N:10][NH:11][C:7]=2[C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)(=[O:42])=[O:41])=[CH:38][CH:39]=1)[CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1446254-t-Amylbenzenesulphonyl chlorideHCID 178510737HCID 178510737, compound

Product 1

HCID 178442204HCID 178442204, compoundYield 30,580.699%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the 2-(5-Pyrazin-2-yl-3-thiophen-2-yl-1H-pyrazol-4-yl)-ethylamine 1D (7 mg, 25.8 μmol), diisopropylethylamine (9.0 μl, 51.6 μmol) and 4-n-pentylbenzenesulfonyl chloride (7.0 mg, 28.3 μmol) in dichloromethane (1 mL) was stirred for 3 h. The reaction mixture was concentrated under reduced pressure. The crude product dissolved in methanol (2 ml) and was purified by prep-HPLC. Removal of the solvent in vacuo provided the title compound (3.8 g mg, 41% yield). MS m/e 481; HPLC retention time 3.54 min (Method A).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe crude product dissolved in methanol (2 ml)
  3. customwas purified by prep-HPLC
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-9245dadad15f431a98c92fe503e58551
Source dataset
uspto-grants-2008_10
Patent number
US07432271B2

Reaction notes

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