HCID 59851160, compound → HCID 59851370, compound

HRID 2373419Notes

Reaction equation

HRID 2373419 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:18]=[C:19]([CH2:23][C:24]#[N:25])[CH:20]=[CH:21][CH:22]=4)[N:14]=[CH:15][C:10]=3[CH2:9][C:8](=[O:26])[NH:7][C:6]=2[CH:27]=1>N.CO.O.[Ni]>[NH2:25][CH2:24][CH2:23][C:19]1[CH:18]=[C:17]([NH:16][C:13]2[N:14]=[CH:15][C:10]3[CH2:9][C:8](=[O:26])[NH:7][C:6]4[CH:27]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=4[C:11]=3[N:12]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 1

HCID 59851160HCID 59851160, compound

Product 1

HCID 59851370HCID 59851370, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of [3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-phenyl]-acetonitrile (I-78) (0.131 g, 0.349 mmol) in saturated NH3 in MeOH solution (50 mL) was added a catalytic amount of Raney 2800 Ni in H2O and the mixture was placed under H2 (50 psi) and stirred for 12 h at 22° C. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo to give crude product as a yellow oil. Purification by C-18 RP LC-MS chromatography afforded I-86 (0.019 g, 14%): MS (AA) Rt═1.25 min, m/z═380 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give crude product as a yellow oil
  4. customPurification by C-18 RP LC-MS chromatography
  5. customafforded I-86 (0.019 g, 14%)

Sources & evidence

ORD record
ord-78eb77c0b4c847a7b85136f7b9af8ded
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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