1,2-Dichloroethane → HCID 86636951, compound

HRID 1366473Notes

Reaction equation

HRID 1366473 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[CH2:29][N:28]([CH3:30])[CH2:27][CH2:26][N:25]1[C:31]1[C:36]([F:37])=[C:35]([NH:38][NH2:39])[N:34]=[C:33]([CH3:40])[N:32]=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:25]3[CH2:26][CH2:27][N:28]([CH3:30])[CH2:29][C@@H:24]3[CH3:23])[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 66935927HCID 66935927, compound

Product 1

HCID 86636951HCID 86636951, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.139 g, 0.45 mmol), 4-[(2S)-2,4-dimethyl-1-piperazinyl]-5-fluoro-6-hydrazino-2-methylpyrimidine (0.118 g, 0.46 mmol), NMM (0.15 mL, 1.38 mmol), HOAt (0.063 g, 0.46 mmol), and EDC (0.088 g, 0.46 mmol) were dissolved in DMF (2 mL). The reaction was stirred overnight. Purified by RP-HPLC to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(2S)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide as a white solid (0.118 g, 47%). LCMS: (M+H)+=542.7.

Workup

  1. customPurified by RP-HPLC

Sources & evidence

ORD record
ord-260032e672c446ebb7f150158e9ebbaf
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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