HCID 44176511, compound → 2-(4-Carbamoylbenzyl)-n-(1-(4-cyanobenzyl)piperidin-4-yl)-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole-8-carboxamide

HRID 340412Notes

Reaction equation

HRID 340412 reaction equation
[C:1]([C:4]1[CH:39]=[CH:38][C:7]([CH2:8][N:9]2[CH2:37][CH2:36][C:12]3[NH:13][C:14]4[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH:23]5[CH2:28][CH2:27][N:26]([C:29](OC(C)(C)C)=O)[CH2:25][CH2:24]5)=[O:21])=[CH:18][C:19]=4[C:11]=3[CH2:10]2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2]>Cl.O1CCOCC1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:37][CH2:36][C:12]3[NH:13][C:14]4[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH:23]5[CH2:24][CH2:25][N:26]([CH2:29][C:7]6[CH:38]=[CH:39][C:4]([C:1]#[N:2])=[CH:5][CH:6]=6)[CH2:27][CH2:28]5)=[O:21])=[CH:18][C:19]=4[C:11]=3[CH2:10]2)=[CH:38][CH:39]=1)(=[O:3])[NH2:2]

Participants

3

Reactant 1

HCID 44176511HCID 44176511, compound

Product 1

HCID 441766182-(4-Carbamoylbenzyl)-n-(1-(4-cyanobenzyl)piperidin-4-yl)-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole-8-carboxamideYield 182.9%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of tert-butyl 4-(2-(4-carbamoylbenzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamido)piperidine-1-carboxylate (28, 745 mg, 1.4 mmol) in 4 N HCl/dioxane (20.0 mL) was allowed to stir at room temperature for 2 h. The reaction mixture was then concentrated to give a tan solid which was triturated with ethyl ether to give 2-(4-carbamoylbenzyl)-N-(1-(4-cyanobenzyl)piperidin-4-yl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide as an off-white solid (700 mg, 99%); MS (ES) 432 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customto give a tan solid which
  3. customwas triturated with ethyl ether

Sources & evidence

ORD record
ord-7297542ee07446d3be865cebbb13e7aa
Source dataset
uspto-grants-2014_11
Patent number
US08895578B2

Reaction notes

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