Diisopropylethylamine → 4-(1-(5-(7,7-Dimethyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile

HRID 541461Notes

Reaction equation

HRID 541461 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2[N:9]=[C:8]([C:11]3[C:12]([CH3:21])=[CH:13][C:14]([CH3:20])=[C:15]([CH:19]=3)[C:16](O)=[O:17])[NH:7][C:6]=2[CH2:5][O:4][CH2:3]1.Cl.[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:22])[C:10]2[N:9]=[C:8]([C:11]3[C:12]([CH3:21])=[CH:13][C:14]([CH3:20])=[C:15]([CH:19]=3)[C:16]([N:24]3[CH2:29][CH2:28][CH:27]([C:30]4[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=[O:17])[NH:7][C:6]=2[CH2:5][O:4][CH2:3]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 193916184-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)2×HCID 682882695-(7,7-Dimethyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)-2,4-dimethylbenzoic acid2×

Product 1

HCID 682887424-(1-(5-(7,7-Dimethyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude 5-(7,7-Dimethyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)-2,4-dimethylbenzoic acid (compound 449.4, 0.086 mmol) was dissolved in DMF (1 mL). 4-(Piperidin-4-yl)benzonitrile hydrochloride (compound 1.5, 19 mg, 0.086 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (HBTU) (65 mg, 0.17 mmol) and DIEA (45 μl, 0.26 mmol) were added and the mixture was stiffed at room temperature for 16 hrs. The mixture was then diluted with ethyl acetate (10 mL) and washed with brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound as a solid foam (15 mg, 30%). m/z (ES+) 469 (M+H)+.

Workup

  1. washwashed with brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3b38b12de3d34f12b41a6e981c9f231b
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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