2-Naphthoyl chloride → Naphthalene-2-carboxylic acid {4-[4-(6-fluoro-benzo[b]thiophen-3-yl)-[1,4]diazepan-1-yl]-butyl}-amide

HRID 1986910노트

반응식

HRID 1986910 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[F:14][C:15]1[CH:16]=[CH:17][C:18]2[C:22]([N:23]3[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH2:25][CH2:24]3)=[CH:21][S:20][C:19]=2[CH:35]=1>N1C=CC=CC=1.C(Cl)Cl>[F:14][C:15]1[CH:16]=[CH:17][C:18]2[C:22]([N:23]3[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)=[O:12])[CH2:25][CH2:24]3)=[CH:21][S:20][C:19]=2[CH:35]=1

참가 물질

4

반응물 2

HCID 752462-Naphthoyl chlorideHCID 577225964-[4-(6-Fluoro-benzo[b]thiophen-3-yl)-[1,4]diazapan-1-yl]butylamine

생성물 1

HCID 10227404Naphthalene-2-carboxylic acid {4-[4-(6-fluoro-benzo[b]thiophen-3-yl)-[1,4]diazepan-1-yl]-butyl}-amide수율 91.9%

시약·촉매·용매 1

HCID 21875418Pyridine methylene chloride용매

실험 절차

Add slowly a solution of 2-naphthoyl chloride (600 mg, 3.15 mmol) to a solution of 4-[4-(6-fluoro-benzo[b]thiophen-3-yl)-[1,4]diazapan-1-yl]butylamine (Example 6) (920 mg, 2.86 mmol), in pyridine-methylene chloride (10 mL,1:1), and stir the solution at room temperature overnight. Evaporate the solvent under vacuum, dissolve the residue in EtOAc and wash the organic layer with water and saturated sodium chloride solution. Combine the organic phases, dry over MgSO4 and evaporate the solvent under vacuum. Purify the crude product by column chromatography (EtOAc/MeOH 7:3) to obtain 1.25 g of a solid LC/MS (LiChrospher 5μ, RP-18, 250 mm CH3CN/Water-gradient 20%→100% (25 min), Flow: 1.5 mL/min) tR=21.11 min, m/z=475.3.

후처리

  1. customEvaporate the solvent under vacuum
  2. dissolutiondissolve the residue in EtOAc
  3. washwash the organic layer with water and saturated sodium chloride solution
  4. dry with materialCombine the organic phases, dry over MgSO4
  5. customevaporate the solvent under vacuum
  6. customPurify the crude product by column chromatography (EtOAc/MeOH 7:3)

출처 및 근거

ORD 기록
ord-065330d01b164a3d91b4402819b85933
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550469B2

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