Diisopropylethylamine → HCID 10459964, compound

HRID 1591937Notes

Reaction equation

HRID 1591937 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([CH2:15][C:16](Cl)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1.Cl.[F:20][C:21]([F:46])([F:45])[C:22]1[CH:23]=[C:24]([S:32]([NH:35][C:36]2[S:37][C:38]3[CH2:39][NH2+:40][CH2:41][CH2:42][C:43]=3[N:44]=2)(=[O:34])=[O:33])[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1.OS([O-])(=O)=O.[Na+]>C(Cl)Cl>[CH:10]1([CH2:15][C:16]([N:40]2[CH2:41][CH2:42][C:43]3[N:44]=[C:36]([NH:35][S:32]([C:24]4[CH:23]=[C:22]([C:21]([F:20])([F:45])[F:46])[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=4)(=[O:34])=[O:33])[S:37][C:38]=3[CH2:39]2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516919Sodium BisulfateHCID 3485182Cyclopentylacetyl chlorideHCID 866088572-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-5-ium hydrochloride

Product 1

HCID 10459964HCID 10459964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIEA and cyclopentyl-acetyl chloride are added at 0° to a mixture of 75 mg of 2-(3,5-bis-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-5-ium hydrochloride salt in CH2Cl2. The mixture obtained is stirred at RT for 4 hours, 2 ml of 1 M aqueous NaHSO4 solution are added and two phases formed are separated. The organic layer obtained is concentrated and subjected to preparative HPLC (RP-18). N-[5-(2-Cyclo-pentyl-acetyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl]-3,5-bis-trifluoromethyl-benzene-sulfonamide is obtained.

Workup

  1. customThe mixture obtained
  2. customtwo phases formed
  3. customare separated
  4. customThe organic layer obtained
  5. concentrationis concentrated

Sources & evidence

ORD record
ord-102f2edf65174196aa4fd45899c31a17
Source dataset
uspto-grants-2007_11
Patent number
US07291734B2

Reaction notes

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