1,2-Dichloroethane → HCID 69315524, compound

HRID 2055656Notes

Reaction equation

HRID 2055656 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:25]([CH3:27])[CH3:26])[C:13]([NH:15][C:16]1[C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=[CH:18][CH:17]=1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH:12]([C:13](=[O:14])[NH:15][C:16]1[CH:17]=[CH:18][N:19]=[CH:20][C:21]=1[C:22](=[O:24])[NH:39][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:25]([CH3:26])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 22172613HCID 22172613, compound

Product 1

HCID 69315524HCID 69315524, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formulae 508 and 509 where R1, R3 and R4 are H; R5 is Benzyl; R6 is Isopropyl; R6′ is H: W, Y and Z are —C═; and X is —N═: A solution of dichloromethane (200 mL), 4-(2-benzyloxycarbonylamino-3-methyl-butyrylamino)-nicotinic acid (10.0 g, 26.9 mmol) and EDC (7.74 g, 40.4 mmol) was stirred at room temperature for 2 hours until the complete consumption of the starting material was observed by reverse phase HPLC. Benzylamine (5.88 mL, 53.8 mmol) was then added and the mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum and purified by silica gel chromatography using hexane-EtOAc (stepwise gradient from 3:1 to 1:2) as eluents to obtain the uncyclized product of Formula 508, [1-(3-benzylcarbamoyl-pyridin-4-ylcarbamoyl)-2-methyl-propyl]carbamic acid benzyl ester (4.45 g, 35.9%) and the cyclized product of Formula 509, [1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[4,3-d]pyrimidin-2-yl)-2-methyl-propyl]-carbamic acid benzyl ester (1.85 g, 15.5%). 508: MS (Cl) M/E: 461.2; 509: MS (Cl) M/E: 443.2.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f8557f99dd994e058f75c41e4540d3b1
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

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