Benzylamine → 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid benzylamide

HRID 1747336Notes

Reaction equation

HRID 1747336 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]([CH2:26][CH2:27][CH3:28])[CH2:22][C:23]([OH:25])=O)[C:13]3=[O:29])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>C1COCC1.O>[CH2:30]([NH:37][C:23](=[O:25])[CH2:22][CH:21]([N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[C:10]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[S:7][CH:8]=2)[C:13]1=[O:29])[CH2:26][CH2:27][CH3:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 251281763-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid

Product 1

HCID 594974523-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid benzylamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (20 mg, 0.049 mmol) in THF (1.0 mL) at room temperature are added benzyl amine (0.027 mL, 0.245 mmol) and 1-hydroxybenzotriazole (32 mg, 0.24 mmol). Then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (40 mg, 0.21 mmol) is added and the reaction mixture is stirred for 16 hr. Water (5 mL) is added and the mixture is extracted with EtOAc (3×10 mL). The organic layers are combined, dried over MgSO4 and concentrated to give crude product. The crude is filtered through a short path of silica gel eluting first with CH2Cl2 then with 50% EtOAc in hexanes to give 23 mg (95%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid benzylamide. LCMS (ESMS): m/z 498.22 (M+H+).

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. filtrationThe crude is filtered through a short path of silica gel eluting first with CH2Cl2

Sources & evidence

ORD record
ord-f596f053973940f79a71afa79a44e52f
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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