Pyridine → N-(5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)methanesulfonamide

HRID 593700Notes

Reaction equation

HRID 593700 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=[CH:15][CH:16]=3)[C:11]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:10][N:9]=2)[CH:5]=[N:6][CH:7]=1.N1C=CC=CC=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH2:25]([NH:24][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])[CH:7]=[N:6][CH:5]=2)=[N:9][N:10]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 904354934-(5-Aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine

Product 1

HCID 86270291N-(5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)methanesulfonamideYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine (60.0 mg, 0.149 mmol) in DCM (20 mL) was added pyridine (0.0241 mL, 0.297 mmol) at room temperature followed by methanesulfonyl chloride (0.0120 mL, 0.149 mmol) and the reaction mixture stirred for 5 h. The volatile components were removed under reduced pressure and the resulting residue was purified by preparative HPLC (Condition 22 as described in general methods) to obtain N-(5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)methanesulfonamide (50.0 mg, 69.8%) as a white solid. LCMS (Condition 4): retention time 2.45 min, [M+1]=482.2. HPLC (Condition 28): retention time=6.83 min, purity 97.53%. 1H NMR (400 MHz, DMSO-d6) δ 2.97 (s, 3 H), 4.51 (d, J=4.8 Hz, 2 H), 5.06 (t, J=4.8 Hz, 1 H), 7.02-7.03 (m, 2 H), 7.22-7.28 (m, 3 H), 7.43-7.52 (m, 5 H), 7.68 (dd, J=2.4 Hz, J=5.6 Hz, 1 H), 7.72 (br s, 1 H), 7.87-7.90 (m, 2 H), 8.35 (br s, 1 H), 8.40 (d, J=1.6 Hz, 1 H), 10.25 (br s, 1 H).

Workup

  1. customThe volatile components were removed under reduced pressure
  2. customthe resulting residue was purified by preparative HPLC (Condition 22 as described in general methods)

Sources & evidence

ORD record
ord-fa84c3843d694650b93a551d946120c0
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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