Diisopropylethylamine → Cyclohexyl 2-{1-[(2,5-dibromophenyl)acetyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate

HRID 1888097Notes

Reaction equation

HRID 1888097 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.CCN(C(C)C)C(C)C.[Cl-].[CH:23]1([O:29][C:30]([C:32]2[N:33]=[C:34]([CH:37]3[CH2:42][CH2:41][NH2+:40][CH2:39][CH2:38]3)[S:35][CH:36]=2)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:40]1[CH2:39][CH2:38][CH:37]([C:34]2[S:35][CH:36]=[C:32]([C:30]([O:29][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[O:31])[N:33]=2)[CH2:42][CH2:41]1)=[O:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 42631952,5-Dibromophenylacetic acidHCID 669115194-{4-[(Cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride

Product 1

HCID 52920338Cyclohexyl 2-{1-[(2,5-dibromophenyl)acetyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2,5-Dibromophenyl)acetic acid (323 mg) and Hünig base (323 mg) are dissolved in dichloromethane (10 ml) and stirred at room temperature for 30 min. 4-{4-[(Cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride (VII-1, 330 mg) is added, and the mixture is stirred for a further 5 min before bromotrispyrrolidinophosphonium hexafluorophosphate (559 mg) is added. The reaction mixture is stirred at room temperature overnight. After removal of the solvent under reduced pressure, the residue is purified chromatographically. This gives cyclohexyl 2-{1-[(2,5-dibromophenyl)acetyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate (250 mg, 43%).

Workup

  1. additionis added
  2. stirringThe reaction mixture is stirred at room temperature overnight
  3. customAfter removal of the solvent under reduced pressure
  4. customthe residue is purified chromatographically

Sources & evidence

ORD record
ord-01a92190da0e45a59a7173a5b24b9d34
Source dataset
uspto-grants-2013_08
Patent number
US08501781B2

Reaction notes

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