Nitrogen → HCID 58299668, compound

HRID 79195Notes

Reaction equation

HRID 79195 reaction equation
FC(F)(F)S(O[C:7]1[N:12]=[N:11][C:10]2[N:13]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:14]3[N:19]=[C:18]([NH2:20])[N:17]=[CH:16][C:15]=3[C:9]=2[CH:8]=1)(=O)=O.N#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(O)=O.CN(C=O)C>[CH:21]1([N:13]2[C:10]3[N:11]=[N:12][CH:7]=[CH:8][C:9]=3[C:15]3[CH:16]=[N:17][C:18]([NH2:20])=[N:19][C:14]2=3)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

9

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 582996927-Amino-9-cyclopentyl-9H-pyrimido[5',4':4,5]pyrrolo[2,3-c]pyridazin-3-yl trifluoromethanesulfonate

Product 1

HCID 58299668HCID 58299668, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

In a 25 mL single-necked round bottom flask were placed compound 318 (94 mg, 234 μmol, palladium diacetate (21 mg, 93 μmol), and 1,1′-bis(diphenylphosphino)ferrocene (130 mg, 234 μmol). The flask was subjected to 3 cycles of evacuation and back-filling with N2. DMF (3 mL) was added under N2 followed by triethylamine (715 μl, 5140 μmol) and formic acid, 98% (176 μl, 4.67 mmol). The resulting mixture was stirred in an oil bath at 65° C. for 1.5 h. The mixture was poured into ice and saturated NaHCO3 aqueous solution and extracted with 10% i-PrOH/DCM (2×). The combined organics were dried over Na2SO4 and concentrated in vacuo. The residue was subjected to combi-flash column chromatography (methanol/DCM with Et3N) to give compound 319 (48 mg, 80% yield) as an reddish solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.08 (1 H, s), 9.01 (1 H, d, J=5.1 Hz), 8.07 (1 H, d, J=5.1 Hz), 7.28 (2 H, s), 5.42 (1 H, quin, J=8.6 Hz), 2.40-2.49 (2 H, m), 1.92-2.14 (4 H, m), 1.63-1.80 (2 H, m). LCMS-ESI (POS), M/Z, M+1: Found 255.1.

Workup

  1. customIn a 25 mL single-necked round bottom flask were placed
  2. extractionextracted with 10% i-PrOH/DCM (2×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-215874c625b04ec3bb2407b0f162ca11
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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