Triethylamine → HCID 67546806, compound

HRID 490624Notes

Reaction equation

HRID 490624 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[CH2:10][CH:9]1[C:31]([OH:33])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[C:44]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)#[N:45].CCN(CC)CC.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[C:14]([O:16][CH2:17][C:18]([Cl:20])([Cl:19])[Cl:21])=[O:15])[CH2:10][CH:9]1[C:31]([N:55]1[CH2:54][CH2:53][N:52]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2[C:44]#[N:45])[CH2:57][CH2:56]1)=[O:33])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735875N-(2-Cyanophenyl)piperazineHCID 67546799HCID 67546799, compound

Product 1

HCID 67546806HCID 67546806, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(2,4-difluoro-benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester (3.5 g, 6.6 mmol), HOBt (1.4 g, 10 mmol), 1-(2-cyanophenyl)piperazine (1.5 g, 7.9 mmol) in DCM (50 ml) were added Et3N (1.8 ml, 13.2 mmol) and EDC.HCl (1.9 g, 10 mmol). The mixture was stirred overnight, then washed with 10% citric acid, Na2CO3, brine, dried and concentrated to give the title product as a colorless oil (4.5 g, 6.4 mmol). MS m/e=700.3 [M+H]+.

Workup

  1. washwashed with 10% citric acid, Na2CO3, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eba5ce325f2d46568bf1e848fa0a4ef6
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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