1-Methylpiperazine → HCID 66547328, compound

HRID 1507995Notes

Reaction equation

[CH3:1][C:2]1([C@H:5]([NH:7][C:8]2[C:9]3[N:10]([CH:17]=[C:18]([C:20]4[O:21][C:22](S(C)=O)=[N:23][N:24]=4)[CH:19]=3)[N:11]=[CH:12][C:13]=2[C:14]([NH2:16])=[O:15])[CH3:6])[CH2:4][CH2:3]1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CN(C=O)C>[CH3:1][C:2]1([C@H:5]([NH:7][C:8]2[C:9]3[N:10]([CH:17]=[C:18]([C:20]4[O:21][C:22]([N:32]5[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]5)=[N:23][N:24]=4)[CH:19]=3)[N:11]=[CH:12][C:13]=2[C:14]([NH2:16])=[O:15])[CH3:6])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 4-((R)-1-(1-methylcyclopropyl)ethylamino)-6-(5-(methylsulfinyl)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (16.00 mg, 0.041 mmol) in NMP (0.5 mL, 0.082M) was added 1-methylpiperazine (20.63 mg, 0.206 mmol) followed with DIPEA (0.029 mL, 0.165 mmol). The solution was stirred at 130° C. for 30 min in a Biotage Initiator microwave. The reaction mixture was dissolved in 1.5 mL of DMF and directly purified on Reverse Phase HPLC to yield desired product (2.65 mg, 15% yield). 1H NMR (599 MHz), δ 8.33 (s, 1H), 8.27 (s, 1H), 7.20 (s, 1H), 3.96-3.89 (m, 1H), 3.63-3.53 (m, 4H), 2.72-2.23 (m, 7H), 1.37 (d, J=6.4 Hz, 3H), 1.23 (s, 3H), 0.68-0.58 (m, 1H), 0.55-0.49 (m, 1H), 0.39 (m, 2H). MS (ES+) m/z: 424.90 (M+H); HPLC: 97%, retention time: 1.70 min (analytical HPLC Method B).

Workup

customdirectly purified on Reverse Phase HPLC

Sources & evidence

ORD record: ord-bd44d1d5c6264820a7e4f562de233db9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221826B2

Reaction notes

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