1,2-Dichloroethane → HCID 86636942, compound

HRID 1366449Notes

Reaction equation

HRID 1366449 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:11][N:12]([CH:21]=[O:22])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:23][C@@H:24]1[N:29]([CH3:30])[CH2:28][CH2:27][N:26]([C:31]2[C:36]([F:37])=[C:35]([NH:38][NH2:39])[N:34]=[C:33]([CH3:40])[N:32]=2)[CH2:25]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH:1]1([CH2:6][C@@H:7]([C:8]([NH:39][NH:38][C:35]2[C:36]([F:37])=[C:31]([N:26]3[CH2:27][CH2:28][N:29]([CH3:30])[C@@H:24]([CH3:23])[CH2:25]3)[N:32]=[C:33]([CH3:40])[N:34]=2)=[O:10])[CH2:11][N:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 66936103HCID 66936103, compound

Product 1

HCID 86636942HCID 86636942, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.184 g, 0.60 mmol), 4-[(3S)-3,4-dimethyl-1-piperazinyl]-5-fluoro-6-hydrazino-2-methylpyrimidine (0.161 g, 0.63 mmol), NMM (0.21 mL, 1.89 mmol), HOAt (0.086 g, 0.63 mmol), and EDC (0.121 g, 0.63 mmol) were dissolved in DMF (4 mL), and the reaction was stirred overnight. Purified by RP-HPLC to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(3S)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.219 g, 64%). LCMS: (M+H)+=542.7.

Workup

  1. customPurified by RP-HPLC

Sources & evidence

ORD record
ord-c5809e44c6ee437181fdf4eae5618fd0
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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