Dimethylformamide → HCID 67134789, compound

HRID 592258Notes

Reaction equation

HRID 592258 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]3)=[CH:19][N:18]=2)=[O:15])=[CH:9][C:8]=1[Cl:32])(=O)=O.[CH3:35][N:36](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:29]([N:26]1[CH2:25][CH2:24][N:23]([C:20]2[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[CH2:13][C:10]3[CH:11]=[CH:12][C:7]([C:35]#[N:36])=[C:8]([Cl:32])[CH:9]=3)=[N:18][CH:19]=2)[CH2:28][CH2:27]1)(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86657958HCID 86657958, compound

Product 1

HCID 67134789HCID 67134789, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(2-(5-(4-acetylpiperazin-1-yl)pyridin-2-ylamino)-2-oxoethyl)-2-chlorophenyl trifluoromethanesulfonate 237-2 (65 mg, 0.125 mmol), Zn(CN)2 (30 mg, 0.255 mmol), Pd(PPh3)4 (14 mg, 0.012 mmol) in DMF (0.6 ml) was stirred at 80° C. under argon for 96 hours. After cooled to room temperature, it was filtered through celite, washed with ethyl acetate, and concentrated by evaporation of solvents. The residue was subjected to reverse phase HPLC purification to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(3-chloro-4-cyanophenyl)acetamide as solid 237-3.

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationit was filtered through celite
  3. washwashed with ethyl acetate
  4. concentrationconcentrated by evaporation of solvents
  5. customphase HPLC purification

Sources & evidence

ORD record
ord-4c2a4a20a6ee43e8abf9910bbdbb442a
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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