Dicyclohexylcarbodiimide → (S)-N-(a-ethylbenzyl)-3-[2-(3-pyridylacetyl)aminoethoxy]-2-phenylquinoline-4-carboxamide

HRID 651072Notes

Reaction equation

HRID 651072 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:3]=1.[CH2:12]([C@H:14]([NH:21][C:22]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:25]=1[O:40][CH2:41][CH2:42][NH2:43])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>>[O:40]([CH:25]([CH3:24])[CH3:26])[CH:41]([CH3:42])[CH3:3].[CH2:12]([C@H:14]([NH:21][C:22]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:25]=1[O:40][CH2:41][CH2:42][NH:43][C:9](=[O:11])[CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 10764865(S)-N-(alpha-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide

Product 2

HCID 7914Diisopropyl EtherHCID 70248862(S)-N-(a-ethylbenzyl)-3-[2-(3-pyridylacetyl)aminoethoxy]-2-phenylquinoline-4-carboxamideYield 116.3%

Procedure

Prepared as described in Example 26 from 0.41 g (2.4 mmol) of 3-pyridylacetic acid hydrochloride, 1.0 g (2.4 mmol) of (S)-N-(α-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide (compound of Description 4), 0.33 ml (2.4 mmol) of TEA, 0.64 g (4.7 mmol) of HOBT and 0.58 g (2.8 mmol) of DCC. The work up and the purification of the reaction mixture were conducted as described in Example 26. After trituration with i-Pr2O, 0.76 g of the title compound were obtained.

Workup

  1. customPrepared
  2. customThe work up and the purification of the reaction mixture

Sources & evidence

ORD record
ord-f4f5199f94874add8aaa04361e31db50
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Reaction notes

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