1,2-Dichloroethane → HCID 86636986, compound

HRID 1366554Notes

Reaction equation

HRID 1366554 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.[Cl:23][C:24]1[NH:25][C:26]([NH:33][CH:34]2[CH2:37][CH2:36][CH2:35]2)=[C:27]([F:32])[C:28](=[N:30][NH2:31])[N:29]=1.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.CCOCC>[Cl:23][C:24]1[N:29]=[C:28]([NH:30][NH:31][C:8](=[O:10])[C@H:7]([CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[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])[C:27]([F:32])=[C:26]([NH:33][CH:34]2[CH2:37][CH2:36][CH2:35]2)[N:25]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 178514348HCID 178514348, compound

Product 1

HCID 86636986HCID 86636986, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.282 g, 0.92 mmol), 2-chloro-6-(cyclobutylamino)-5-fluoro-4(1H)-pyrimidinone hydrazone (0.225 g), HOAt (0.132 g, 0.97 mmol) and NMM (0.53 mL, 4.85 mmol) in DMF (5 mL) was added EDC (0.186 g, 0.97 mmol) and the reaction was stirred overnight. The mixture was diluted with ether, washed with water, and the aqueous layer was back extracted with ether. The organics were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by RP-HPLC to provide [(2R)-3-{2-[2-chloro-6-(cyclobutylamino)-5-fluoro-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide as a brown oil (0.055 g). LCMS: (M+H)+=519.2.

Workup

  1. washwashed with water
  2. extractionthe aqueous layer was back extracted with ether
  3. dry with materialThe organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-143e64e6bdbe4da7911beeda44a38035
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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