1,2-Dichloroethane → HCID 86636999, compound

HRID 1366599Notes

Reaction equation

HRID 1366599 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:11][N:12]([CH:21]=[O:22])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:23][C:24]1[C:25]([N:33]([CH3:42])[CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)=[N:26][C:27]([CH3:32])=[N:28][C:29]=1[NH:30][NH2:31].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[CH:1]1([CH2:6][C@@H:7]([C:8]([NH:31][NH:30][C:29]2[C:24]([F:23])=[C:25]([N:33]([CH3:42])[CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)[N:26]=[C:27]([CH3:32])[N:28]=2)=[O:10])[CH2:11][N:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 66936254HCID 66936254, compound

Product 1

HCID 86636999HCID 86636999, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (230 mg, 0.76 mmol), 5-fluoro-6-hydrazino-N,2-dimethyl-N-[2-(4-pyridinyl)ethyl]-4-pyrimidinamine (210 mg, 0.76 mmol), EDC (180 mg, 0.91 mmol), HOAt (120 mg, 0.91 mmol), and NMM (0.25 mL, 2.28 mmol) in 5 ml DMF was stirred at room temperature overnight. The reaction mixture was then purified via reverse phase HPLC to provide {(2R)-2-(cyclopentylmethyl)-3-[2-(5-fluoro-2-methyl-6-{methyl[2-(4-pyridinyl)ethyl]amino}-4-pyrimidinyl)hydrazino]-3-oxopropyl}[(phenylmethyl)oxy]formamide (290 mg, 67%). LCMS: (M+H)+: 564.3.

Workup

  1. customThe reaction mixture was then purified via reverse phase HPLC

Sources & evidence

ORD record
ord-694cf6d0227540dfa8f2dad4da172d86
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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