1,2-Dichloroethane → HCID 86637001, compound

HRID 1366603Notes

Reaction equation

HRID 1366603 reaction equation
Cl.Cl.[Cl:3][C:4]1[NH:5][C:6]([NH:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[C:7]([F:12])[C:8](=[N:10][NH2:11])[N:9]=1.[CH:20]1([CH2:25][C@H:26]([CH2:30][N:31]([CH:39]=[O:40])[O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[C:27](O)=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:3][C:4]1[N:9]=[C:8]([NH:10][NH:11][C:27](=[O:28])[C@H:26]([CH2:25][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:30][N:31]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH:39]=[O:40])[C:7]([F:12])=[C:6]([NH:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[N:5]=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 178478860HCID 178478860, compound

Product 1

HCID 86637001HCID 86637001, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-fluoro-6-[(1,3-thiazol-2-ylmethyl)amino]-4(1H)-pyrimidinone hydrazone dihydrochloride (0.3052 g, 0.882 mmol) and (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (0.457 g, 1.059 mmol) were dissolved in DMF (8 mL). NMM (0.58 mL, 5.2753 mmol) was added, followed by HOAt (0.144 g, 1.059 mmol) and EDC (0.203 g, 1.059 mmol). After stirring overnight, the reaction mixture was purified by RP-HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1,3-thiazol-2-yl methyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide as a beige solid (0.3031 g, 62%). LCMS: (M+H)+=556.2.

Workup

  1. customthe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-4468f0cee7e542838d20801c0ac8453f
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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