1,2-Dichloroethane → [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide

HRID 1366464Notes

Reaction equation

HRID 1366464 reaction equation
[F:1][C:2]1[C:3](=[N:17][NH2:18])[N:4]=[C:5]([CH3:16])[NH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH:19]1([CH2:24][C@H:25]([CH2:29][N:30]([CH:39]=[O:40])[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:26](O)=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH:19]1([CH2:24][C@@H:25]([C:26]([NH:18][NH:17][C:3]2[C:2]([F:1])=[C:7]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)[N:6]=[C:5]([CH3:16])[N:4]=2)=[O:27])[CH2:29][N:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:39]=[O:40])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 178433366HCID 178433366, compound

Product 1

HCID 86636947[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamideYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4(1H)-pyrimidinone hydrazone (0.0954 g, 0.3846 mmol) and (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.141 g, 0.4622 mmol) were dissolved in DMF (3 mL). NMM (0.13 mL, 1.1824 mmol) was added, followed by HOAt (0.063 g, 0.4632 mmol) and EDC (0.088 g, 0.459 mmol). After stirring overnight the reaction mixture was purified by RP-HPLC to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide as a white solid (0.0999 g, 48%). LCMS: (M+H)+=536.3.

Workup

  1. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-a641609df31b4f8aaad246649ce57534
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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