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

HRID 1986910Notes

Reaction equation

HRID 1986910 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-065330d01b164a3d91b4402819b85933
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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