Cyanoacetamide → HCID 58084346, compound

HRID 1853135Notes

Reaction equation

HRID 1853135 reaction equation
[C:1]([O:5][C:6]([N:8]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:9]1[C:10]([C:16]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:19]3[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:18]=3[N:17]=2)=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:40]([CH2:42][C:43]([NH2:45])=[O:44])#[N:41].C1(P(C2C=CC=CC=2)C2C=CC=C3C=2OC2C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=2C3(C)C)C=CC=CC=1.C1(C=CC(=O)C=CC2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:9]1[C:10]([C:16]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:19]3[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:18]=3[N:17]=2)=[N:11][C:12]([NH:45][C:43](=[O:44])[CH2:42][C:40]#[N:41])=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 7898CyanoacetamideHCID 10796Cesium carbonateHCID 95417Dibenzylidene acetoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86661948HCID 86661948, compound

Product 1

HCID 58084346HCID 58084346, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-[3-(bis(tert-butoxycarbonyl)amino)-6-bromo-pyrazin-2-yl]-6-methyl-benzimidazole-1-carboxylate (150 mg, 0.2481 mmol), 2-cyanoacetamide (31.28 mg, 0.3722 mmol), (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (8.616 mg, 0.01489 mmol) and 1,5-diphenylpenta-1,4-dien-3-one; palladium (4.544 mg, 0.004962 mmol) heated with dicesium carbonate (161.7 mg, 0.4962 mmol) in dioxane for 4 hours at 60° C. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography eluting with 20% EtOAc/petroleum ether to give the sub-title product as pale yellow solid which was used directly in the next step.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluting with 20% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-9786a7f1ce194fcca72e1dee81bc339d
Source dataset
uspto-grants-2015_02
Patent number
US08962631B2

Reaction notes

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