Propylene Oxide → HCID 10094737, compound

HRID 1795461Notes

Reaction equation

HRID 1795461 reaction equation
[CH3:1][N:2]1[C:7]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:6][C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:4]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[C:3]1=[O:29].CN1C(=O)C(C2C=CC3C(=CC=CC=3)C=2)=C(C2C=CN=CC=2)C=C1C1CCNCC1.[CH3:60][CH:61]1[CH2:63][O:62]1>CN(C=O)C>[OH:62][CH:61]([CH3:63])[CH2:60][N:10]1[CH2:11][CH2:12][CH:8]([C:7]2[N:2]([CH3:1])[C:3](=[O:29])[C:4]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[C:5]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:6]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 22185184HCID 22185184, compoundHCID 69588867HCID 69588867, compound

Product 1

HCID 10094737HCID 10094737, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-methyl-3-naphthalen-2-yl-6-pyrrolidin-3-yl-1H-[4,4′]bipyridinyl-2-one (prepared following the same method as described for 1′-methyl-5′-naphthalen-2-yl-1,2,3,4,5,6-hexahydro-1′H-[4,2′;4′,4″]terpyridin-6′-one, Scheme 12) (0.5 g, 1.3 mmol) in dry DMF (5 mL) was added 2-methyl-oxirane (2.6 mmol, 150 mg) and then heated at 80° C. for 5 h. After cooling down to RT the solvent was removed under vacuum and the residue was purified by flash chromatography (2%, 2M methanol ammonia in DCM) to obtain the title compound (150 mg, 26%) as a yellow solid. MS (ES+): 440 (M+H)+.

Workup

  1. temperatureAfter cooling down to RT the solvent
  2. customwas removed under vacuum
  3. customthe residue was purified by flash chromatography (2%, 2M methanol ammonia in DCM)

Sources & evidence

ORD record
ord-b478759b3042425e862c1f112af94da6
Source dataset
uspto-grants-2006_04
Patent number
US07026326B2

Reaction notes

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