Dimethylacetamide → 4-{3-[4-(4-Carbamoyl-benzo[b]thiophen-2-yl)-5-chloro-pyrimidin-2-ylamino]-propyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 1986306Notes

Reaction equation

HRID 1986306 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12]C(CCCN)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:19]1[N:24]=[C:23]([C:25]2[S:29][C:28]3[CH:30]=[CH:31][CH:32]=[C:33]([C:34]([NH2:36])=[O:35])[C:27]=3[CH:26]=2)[C:22]([Cl:37])=[CH:21][N:20]=1.[CH:38]([N:41](C(C)C)CC)(C)C.[CH3:47][C:48]([N:50](C)C)=O>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:41]([CH2:38][CH2:47][CH2:48][NH:50][C:19]2[N:24]=[C:23]([C:25]3[S:29][C:28]4[CH:30]=[CH:31][CH:32]=[C:33]([C:34](=[O:35])[NH2:36])[C:27]=4[CH:26]=3)[C:22]([Cl:37])=[CH:21][N:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 22990164tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylateHCID 866253572-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid amide

Product 1

HCID 688587304-{3-[4-(4-Carbamoyl-benzo[b]thiophen-2-yl)-5-chloro-pyrimidin-2-ylamino]-propyl}-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(3-Aminopropyl)-piperidine-1-carboxylic acid tert-butyl ester (0.818 g, 3.36 mmol) is added to a stirred suspension of 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid amide (0.436 g, 1.34 mmol) and diisopropylethylamine (0.70 mL, 4.0 mmol) in anhydrous 1,4-dioxane (8 mL) and dimethylacetamide (2 mL) at room temperature under nitrogen. The resultant mixture is heated in an oil bath at 95° C. for 7 hours. At room temperature the mixture is concentrated and chromatographed on silica gel, eluting with CH3OH in dichloromethane: 0-6%, to give 4-{3-[4-(4-carbamoyl-benzo[b]thiophen-2-yl)-5-chloro-pyrimidin-2-ylamino]-propyl}-piperazine-1-carboxylic acid tert-butyl ester (0.403 g) as a solid.

Workup

  1. concentrationAt room temperature the mixture is concentrated
  2. customchromatographed on silica gel
  3. washeluting with CH3OH in dichloromethane

Sources & evidence

ORD record
ord-f837eba8581b49fd9a0ca93a26fb2b8d
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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