Ammonia → 5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinamide

HRID 593705Notes

Reaction equation

[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[N:10][N:11]=[C:12]3[C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:27]=2)[C:22]([O:24]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:36]>CO>[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[N:10][N:11]=[C:12]3[C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:27]=2)[C:22]([NH2:36])=[O:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate (230 mg, 0.288 mmol) in MeOH (5 mL) was purged with ammonia gas for 5 minutes at −10° C. The reaction mixture was heated in a sealed tube at 70° C. for 12 h. The volatile components were removed under reduced pressure and the resulting residue was purified by HPLC (Condition 20 as described in general methods) to afford 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinamide (50.0 mg, 39.8%) as a yellow solid. LCMS (Condition 2): retention time 1.90 min, [M+1]=433.0. HPLC (Condition 25): retention time=5.20 min, purity 98.63%. 1H NMR (400 MHz, DMSO-d6) δ 4.66 (d, J=4.0 Hz, 2 H), 6.32 (dd, J=4.0 Hz, J=4.4 Hz, 1 H), 7.22-7.24 (m, 1 H), 7.28 (d, J=7.6 Hz, 1 H), 7.51-7.60 (m, 5 H), 7.68-7.73 (m, 3 H), 7.84 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 7.93 (dd, J=7.2 Hz, J=8.4 Hz, 1 H), 8.22-8.24 (m, 1 H), 8.28 (br s, 1 H), 8.51 (t, J=2.0 Hz, 1 H), 8.99 (d, J=2.0 Hz, 1H), 9.18 (d, J=2.0 Hz, 1 H).

Workup

customThe volatile components were removed under reduced pressure
customthe resulting residue was purified by HPLC (Condition 20 as described in general methods)

Sources & evidence

ORD record: ord-470c4f78515c418bb9a83875c0b3be26
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242966B2

Reaction notes

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