Dibromomethane → 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acid

HRID 2245597

반응식

HRID 2245597 반응식
ClC(Cl)C(O)=O.N[C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=3)[C:31]([CH:40]3[CH2:42][CH2:41]3)=[CH:30][CH:29]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1.N([O-])=O.[Na+].[Br:47]CBr>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:47][C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=3)[C:31]([CH:40]3[CH2:42][CH2:41]3)=[CH:30][CH:29]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1

참가 물질

6

반응물 4

HCID 3024DibromomethaneHCID 6597Dichloroacetic AcidHCID 23668193Sodium NitriteHCID 598131054-[2-(5-amino-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acid

생성물 1

HCID 162218174-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acid수율 40%

시약·촉매·용매 1

HCID 165294Benzyltriethylammonium bromide촉매

실험 절차

Dichloroacetic acid (0.063 mL, 0.76 mmol) was added to a mixture of compound 12 (200 mg, 0.38 mmol), benzyltriethyl ammonium bromide (311 mg, 1.14 mmol) and sodium nitrite (526 mg, 7.63 mmol) in dibromomethane (3 mL). The mixture was stirred at room temperature for 18 hours in the dark. The reaction mixture was then concentrated and the resulting residue was purified by prep. TLC (95% dichloromethane/5% methanol) to afford 90.4 mg of 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acid (13), 40% yield.

후처리

  1. concentrationThe reaction mixture was then concentrated
  2. customthe resulting residue was purified by prep

출처 및 근거

ORD 기록
ord-3b0fb3a561ea40e8a12ea9c7dbd45c8a
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683087B2

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