2-Pyridinemethanamine → Ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate

HRID 593704Notes

Reaction equation

HRID 593704 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH:26]=2)[C:23]([O-:25])=[O:24])=[N:4][N:3]=1.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1.[C:35](NS(C1C=NC=C(C2C3C(=C(C4C=CC=CC=4)C=CC=3)C(NCC3C=CC=CN=3)=NN=2)C=1)(=O)=O)(C)(C)[CH3:36]>>[C:12]1([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:11]=2[C:2]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[N:3][N:4]=[C:5]3[C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH:26]=2)[C:23]([O:25][CH2:35][CH3:36])=[O:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 195092-PyridinemethanamineHCID 90423975N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamideHCID 1317345635-(4-Chloro-5-phenylphthalazin-1-yl)nicotinate

Product 1

HCID 90424789Ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinateYield 88%

Procedure

Ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate (3.10 g, 88.0%, brown solid) was prepared from 5-(4-chloro-5-phenylphthalazin-1-yl)nicotinate (3.00 g, 7.70 mmol) and 2-(aminomethyl)pyridine (10.0 mL, 97.0 mmol) by the methods described for the preparation of N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide in Example 1. The residue was purified by preparative HPLC (Condition 15 as described in general methods). LCMS (Condition 2): retention time 1.90 min, [M+1]=462.2. HPLC (Condition 25): retention time=7.06 min, purity 96.07%. 1H NMR (400 MHz, DMSO-d6) δ 1.38 (t, J=7.2 Hz, 3 H), 4.42 (q, J=7.2 Hz, 2 H), 4.67 (d, J=4.4 Hz, 2 H), 6.35 (dd, J=4.0 Hz, J=4.4 Hz, 1 H), 7.21-7.25 (m, 1 H), 7.28 (d, J=8.0 Hz, 1 H), 7.50-7.61 (m, 5 H), 7.69-7.73 (m, 2 H), 7.84 (dd, J=1.6 Hz, J=8.4 Hz, 1 H), 7.93 (dd, J=7.2 Hz, J=8.4 Hz, 1 H), 8.23 (dt, J=0.8 Hz, J=4.8 Hz, 1 H), 8.53 (t, J=2.0 Hz, 1 H), 9.11 (d, J=2.0 Hz, 1 H), 9.24 (d, J=2.0 Hz, 1 H).

Workup

  1. customThe residue was purified by preparative HPLC (Condition 15 as described in general methods)

Sources & evidence

ORD record
ord-4f4082d581b54b8a873cf6f30893bf19
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

Loading…