Ammonium Hydroxide → HCID 44232009, compound

HRID 1259142Notes

Reaction equation

HRID 1259142 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]=2[N:3]=1.[OH-].[NH4+]>C(O)C.[Ni]>[NH2:19][CH2:18][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]2=[N:3][C:2]=3[NH2:1])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 58213676HCID 58213676, compound

Product 1

HCID 44232009HCID 44232009, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)benzonitrile (from the previous step) in ethanol and ammonium hydroxide (4:1, 0.2 M) stirred at room temperature was added raney nickel (10 eq). The reaction mixture was stirred under hydrogen atmosphere until the conversion was complete as shown by TLC. The reaction mixture was filtered through a short celite pad. The celite pad was washed with EtOAc. Combined organic extracts were concentrated under vacuum and the resulting crude residue was purified by chromatography (silica gel, 50-100% EtOAc in hexanes) to afford product 2-(4-(aminomethyl)phenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine. 1H NMR of the TFA salt: (methanol-d4): δ 8.81 (d, 1H), 8.79 (d, 1H), 8.38 (d, 1H), 7.51 (s, 1H), 7.44 (dd, 1H), 7.36 (dd, 4H), 4.07 (s, 2H), 3.29 (s, 2H), 3.20-3.14 (dd, 2H), 2.55 (s, 3H). LRMS [M+H]=343.2

Workup

  1. filtrationThe reaction mixture was filtered through a short celite pad
  2. washThe celite pad was washed with EtOAc
  3. concentrationCombined organic extracts were concentrated under vacuum
  4. customthe resulting crude residue was purified by chromatography (silica gel, 50-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e0aa79dfa28a45b6a83ddec10a0bfb41
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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