Pyridine → Isopropyl (5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)carbamate

HRID 593701Notes

Reaction equation

HRID 593701 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.[C:38](Cl)(=[O:43])[O:39][CH:40]([CH3:42])[CH3:41]>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][C:38](=[O:43])[O:39][CH:40]([CH3:42])[CH3:41])[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 7917Isopropyl chloroformateHCID 904354934-(5-Aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine

Product 1

HCID 86270292Isopropyl (5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)carbamateYield 68.7%

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 (0.241 mL, 0.297 mmol) at room temperature followed by isopropyl carbonochloridate (18.2 mg, 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 23 as described in general methods) to afford isopropyl (5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)carbamate (50.0 mg, 68.7%) as a white solid. LCMS (Condition 4): retention time 2.60 min, [M+1]=490.2. HPLC (Condition 28): retention time=7.65 min, purity 99.27%. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (d, J=6.4 Hz, 6 H), 4.51 (d, J=4.8 Hz, 2 H), 4.93 (sept, J=6.4 Hz, 1 H), 5.06 (dd, J=4.8 Hz, J=5.2 Hz, 1 H), 7.01-7.03 (m, 2 H), 7.21-7.28 (m, 3 H), 7.42-7.52 (m, 5 H), 7.69 (dd, J=1.2 Hz, J=6.8 Hz, 1 H), 7.85-7.93 (m, 2 H), 8.16 (br s, 1 H), 8.47 (d, J=1.6 Hz, 1 H), 8.80 (d, J=2.4 Hz, 1 H), 10.00 (s, 1 H).

Workup

  1. customThe volatile components were removed under reduced pressure
  2. customthe resulting residue was purified by preparative HPLC (Condition 23 as described in general methods)

Sources & evidence

ORD record
ord-19b16e8dc35c41e1ae88c02ea76519b7
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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