4-Methylmorpholine → N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide

HRID 2055169Notes

Reaction equation

HRID 2055169 reaction equation
[CH2:1]([O:8][N:9]([CH2:12][C:13]1([C:18]([OH:20])=O)[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]([C:23]1[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=1)[NH2:22].CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[CH2:1]([O:8][N:9]([CH2:12][C:13]1([C:18]([NH:22][NH:21][C:23]2[N:28]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:26]=[CH:25][N:24]=2)=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17]1)[CH:10]=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 181649HOAtHCID 12680792-Hydrazino-4-(trifluoromethyl)pyrimidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 714169851-{[(Benzyloxy)(formyl)amino]methyl}cyclopentane-1-carboxylic acid

Product 1

HCID 86606471N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamideYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-[(Benzyloxy-formyl-amino)-methyl]-cyclopentanecarboxylic acid (0.10 g, 0.36 mmol), 2-hydrazino-4-(trifluoromethyl)pyrimidine (0.10 g, 0.43 mmol), NMM (0.11 g, 1.08 mmol) and HOAt (0.059 g, 0.43 mmol) in DMF (2 mL) at room temperature was added 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (0.085 g, 0.43 mmol). After stirring at room temperature 18 h, the reaction mixture was then purified by preparative, reverse-phase HPLC to afford the title compound as a white solid (0.085 g, 57%). MH+438.

Workup

  1. customthe reaction mixture was then purified by preparative, reverse-phase HPLC

Sources & evidence

ORD record
ord-e450fe8d6bae461b9194caa733f08bc7
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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