HCID 89473219, compound → HCID 117600717, compound

HRID 931637Notes

Reaction equation

HRID 931637 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@:15]3([CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:22])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1>[Pd].CO.CCOC(C)=O>[O:18]1[CH2:19][CH2:20][C@:15]2([C:4]3[C:5](=[N:6][CH:7]=[CH:2][CH:3]=3)[O:8][C:9]3[C:14]2=[CH:13][C:12]([NH2:22])=[CH:11][CH:10]=3)[N:16]=[C:17]1[NH2:21]

Participants

5

Reactant 1

HCID 89473219HCID 89473219, compound

Product 1

HCID 117600717HCID 117600717, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 15-mL flask was charged with (S)-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.015 g, 0.042 mmol) and 10% palladium on carbon (0.075 g, 0.706 mmol). The material was suspended in MeOH (1.5 mL) and EtOAc (0.5 mL). The reaction was stirred for 2 h at rt under an atmosphere of hydrogen. The mixture was filtered through Celite, rinsing with 10% MeOH-dcm, and the filtrate was concentrated to afford crude (S)-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (8 mg, 0.028 mmol).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washrinsing with 10% MeOH-dcm
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-91c4d9c0e58741f7a063b2a10af681b3
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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