1,2-Dichloroethane → HCID 86636979, compound

HRID 1366535Notes

Reaction equation

HRID 1366535 reaction equation
Cl.Cl.Cl.Cl.Cl.[Cl:6][C:7]1[N:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH:15]([N:18]([CH3:20])[CH3:19])[C:14]2([CH3:22])[CH3:21])[C:10]([F:23])=[C:9]([NH:24][NH2:25])[N:8]=1.[CH:26]1([CH2:31][C@H:32]([CH2:36][N:37]([CH:46]=[O:47])[O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:33](O)=[O:34])[CH2:30][CH2:29][CH2:28][CH2:27]1.CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C>[Cl:6][C:7]1[N:8]=[C:9]([NH:24][NH:25][C:33](=[O:34])[C@H:32]([CH2:31][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:36][N:37]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:46]=[O:47])[C:10]([F:23])=[C:11]([N:13]2[CH2:17][CH2:16][CH:15]([N:18]([CH3:20])[CH3:19])[C:14]2([CH3:21])[CH3:22])[N:12]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 131728711HCID 131728711, compound

Product 1

HCID 86636979HCID 86636979, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of racemic 1-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N,2,2-tetramethyl-3-pyrrolidinamine pentahydrochloride (0.3649 g, 0.752 mmol) in DMF (5 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.2140 g, 0.701 mmol), N-methylmorpholine (0.770 mL, 7.00 mmol), 1-hydroxy-7-azabenzotriazole (114 mg, 0.838 mmol), and EDC (161 mg, 0.840 mmol). The solution was stirred overnight and purified directly by Gilson RPLC to provide [(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1755 g, 42% yield, mixture of diastereomers) as a brown oil. LCMS: (M+H)+: 590.4.

Workup

  1. custompurified directly by Gilson RPLC

Sources & evidence

ORD record
ord-050d967ff08442e69fffa9cd26c3c6ab
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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