1,2-Dichloroethane → HCID 86637021, compound

HRID 1366654Notes

Reaction equation

HRID 1366654 reaction equation
[Cl:1][C:2]1[NH:3][C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)=[C:5]([F:10])[C:6](=[N:8][NH2:9])[N:7]=1.[CH:19]1([CH2:24][C@H:25]([CH2:29][N:30]([CH:38]=[O:39])[O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]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>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:26](=[O:27])[C@H:25]([CH2:24][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:29][N:30]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH:38]=[O:39])[C:5]([F:10])=[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[N:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 57937086(2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acidHCID 178514353HCID 178514353, compound

Product 1

HCID 86637021HCID 86637021, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-fluoro-6-{[2-(3-thienyl)ethyl]amino}-4(1H)-pyrimidinone hydrazone as a brown sticky solid (0.1401 g) and (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (0.253 g, 0.586 mmol) were dissolved in DMF (7 mL). NMM (0.27 mL, 2.90 mmol) was added, followed by HOAt (0.080 g, 0.588 mmol) and EDC (0.112 g, 0.584 mmol). After stirring overnight, the reaction mixture was purified by RP-HPLC to provide [(2R)-3-[2-(2-chloro-5-fluoro-6-{[2-(3-thienyl)ethyl]amino}-4-pyrimidinyl)hydrazino]-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide as an orange solid (0.1677 g). LCMS: (M+H)+=569.3.

Workup

  1. customthe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-4a34143e276744258524ced6583b7e36
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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