1,2-Dichloroethane → HCID 86636968, compound

HRID 1366509Notes

Reaction equation

HRID 1366509 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([N:9]2[CH2:15][CH:14]([N:16]([CH3:18])[CH3:17])[C:11]3([CH2:13][CH2:12]3)[CH2:10]2)[C:6]([F:19])=[C:5]([NH:20][NH2:21])[N:4]=1)[CH3:2].[CH:22]1([CH2:27][C@H:28]([CH2:32][N:33]([CH:42]=[O:43])[O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:29](O)=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23]1.CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C>[CH:22]1([CH2:27][C@@H:28]([C:29]([NH:21][NH:20][C:5]2[C:6]([F:19])=[C:7]([N:9]3[CH2:15][CH:14]([N:16]([CH3:17])[CH3:18])[C:11]4([CH2:12][CH2:13]4)[CH2:10]3)[N:8]=[C:3]([CH2:1][CH3:2])[N:4]=2)=[O:30])[CH2:32][N:33]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:42]=[O:43])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 66936056HCID 66936056, compound

Product 1

HCID 86636968HCID 86636968, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of racemic 5-(2-ethyl-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N-dimethyl-5-azaspiro[2.4]heptan-7-amine (0.0818 g, 0.278 mmol) in DMF (3 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.0778 g, 0.255 mmol), N-methylmorpholine (0.140 mL, 1.273 mmol), 1-hydroxy-7-azabenzotriazole (42 mg, 0.309 mmol), and EDC (59 mg, 0.308 mmol). The solution was stirred overnight and then purified directly by Gilson RPLC to give [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[7-(dimethylamino)-5-azaspiro[2.4]hept-5-yl]-2-ethyl-5-fluoro-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1058 g, 71% yield, mixture of diastereomers) as a yellow oil. LCMS: (M+H)+: 582.3.

Workup

  1. custompurified directly by Gilson RPLC

Sources & evidence

ORD record
ord-3f57e9dc8d6542058adb88afeb633758
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…