HCID 86654729, compound → HCID 86654730, compound

HRID 2092840Notes

Reaction equation

HRID 2092840 reaction equation
I[C:2]1[C:3]2[CH2:33][NH:32][C:31](=[O:34])[C:4]=2[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[C:35]([Zn]C#N)#[N:36]>[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C)C(=O)C>[C:35]([C:2]1[C:3]2[CH2:33][NH:32][C:31](=[O:34])[C:4]=2[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])#[N:36]

Participants

7

Reactant 2

HCID 86654729HCID 86654729, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 86654730HCID 86654730, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To an oven-dried microwave vial was added tert-butyl (1S,2R)-2-(7-iodo-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (47.0 mg, 0.081 mmol), dicyanozinc (5.74 mg, 0.049 mmol), zinc powder (0.532 mg, 8.14 μmol), dppf (0.451 mg, 0.814 μmol), and Pd2(dba)3 (0.745 mg, 0.814 μmol). N,N-Dimethylacetamide (814 μL) was added and the resulting dark brown solution was degassed with nitrogen for 3 min. The vial was capped and heated at 80° C. with stirring for 1 h. The temperature was increased to 110° C., and the mixture was stirred for an additional 3 h, then cooled to RT, diluted with EtOAc (10 mL), and washed with water (2×10 mL) and brine (10 mL). The organic phase was dried with sodium sulfate and concentrated to give the title compound as a brown residue, which was used without further purification (40 mg, 103%). [M+H] calc'd for C26H32N6O3, 477. found, 477.

Workup

  1. customthe resulting dark brown solution was degassed with nitrogen for 3 min
  2. customThe vial was capped
  3. temperatureThe temperature was increased to 110° C.
  4. stirringthe mixture was stirred for an additional 3 h
  5. temperaturecooled to RT
  6. additiondiluted with EtOAc (10 mL)
  7. washwashed with water (2×10 mL) and brine (10 mL)
  8. dry with materialThe organic phase was dried with sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-877b9e2ef65942768664fc67f81a7087
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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