2-Propanamine, 1-methoxy-, (2S)- → (S)-3-[2-(2-Methoxy-1-methyl-ethylamino)-pyrimidin-4-yl]-2-o-tolyloxy-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 1455242Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]2[N:15]3[CH2:16][CH2:17][CH2:18][N:14]3[C:13](=[O:19])[C:12]=2[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:28][O:29][CH2:30][C@@H:31]([NH2:33])[CH3:32]>C1(C)C=CC=CC=1>[CH3:28][O:29][CH2:30][C@@H:31]([NH:33][C:5]1[N:10]=[C:9]([C:11]2[N:15]3[CH2:16][CH2:17][CH2:18][N:14]3[C:13](=[O:19])[C:12]=2[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH:8]=[CH:7][N:6]=1)[CH3:32]

Participants

Conditions

Temperature: 115 °C

Procedure

To a solution of 3-(2-methanesulfonyl-pyrimidin-4-yl)-2-o-tolyloxy-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 3, (0.11 g, 0.28 mmol) in toluene (4 mL) is added (S)-1-methoxy-2-propylamine (0.10 g, 1.13 mmol). The reaction mixture is heated to 115° C. for 24 h. The solvent is removed in vacuo and the resulting residue is purified by preparative HPLC to afford 52 mg of the desired product as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.28 (d, J=5.1 Hz, 1H), 7.22 (d, J=7.2 Hz, 1H), 7.16 (d, J=5.4 Hz, 1H), 7.09 (t, J=7.5 Hz, 1H), 6.97 (t, J=7.5 Hz, 1H), 6.83 (d, J=7.5 Hz, 1H), 4.29-4.21 (m, 1H), 4.17 (t, J=7.2 Hz, 2H), 4.01 (t, J=7.2 Hz, 2H), 3.50 (dddd, J=9.3, 9.3, 4.5, 4.5 Hz, 2H), 3.42 (s, 3H), 2.69 (dt, J=7.2 Hz, 2H), 2.46 (s, 3H), 1.31 (d, J=6.6 Hz, 3H); ESI+ MS: m/z (rel intensity) 396.2 (90, M++H); Anal Calcd for C21H25N5O3: C, 63.78; H, 6.37; N, 17.71. Found: C, 63.63; H, 6.20; N, 17.05.

Workup

customThe solvent is removed in vacuo
customthe resulting residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-61c7f3d49de644518e79282fd9b9aade
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482356B2

Reaction notes

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