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

HRID 1888097ノート

反応式

HRID 1888097 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-01a92190da0e45a59a7173a5b24b9d34
出典データセット
uspto-grants-2013_08
特許番号
US08501781B2

反応ノート

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