Potassium Carbonate → 2-(3-Methylisothiazol-5-ylamino)-4-(2-oxoazepan-3-ylamino)benzonitrile

HRID 84874Notes

Reaction equation

HRID 84874 reaction equation
Br[C:2]1[CH:9]=[C:8]([NH:10][CH:11]2[CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]2=[O:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:20][C:21]1[S:25][N:24]=[C:23]([CH3:26])[CH:22]=1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:26][C:23]1[CH:22]=[C:21]([NH:20][C:2]2[CH:9]=[C:8]([NH:10][CH:11]3[CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]3=[O:18])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[S:25][N:24]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 675087722-Bromo-4-(2-oxoazepan-3-ylamino)benzonitrile

Product 1

HCID 675082872-(3-Methylisothiazol-5-ylamino)-4-(2-oxoazepan-3-ylamino)benzonitrileYield 159.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-bromo-4-(2-oxoazepan-3-ylamino)benzonitrile (81 mg, 0.263 mmol), 5-amino-3-methylisothiazole hydrochloride (63 mg, 0.418 mmol), K2CO3 (120 mg, 0.869 mmol), BINAP (40 mg, 0.064 mmol) and Pd(OAc)2 (20 mg, 0.089 mmol) in dioxane (3 mL) was degassed with argon, then was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo to give 2-(3-methylisothiazol-5-ylamino)-4-(2-oxoazepan-3-ylamino)benzonitrile (143 mg)

Workup

  1. customwas degassed with argon
  2. additionWater and EtOAc were added
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd4a72ebb13846df8c32731ec3f3c230
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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