Cyclopropylamine → HCID 89783319, compound
Reaction equation
F[C:2]1[C:3]([CH3:24])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[C:18]4([CH2:22][CH2:21]4)[CH2:17][NH:16][C:15](=[O:23])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH:25]1([NH2:28])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>>[CH:25]1([NH:28][C:2]2[C:3]([CH3:24])=[N:4][C:5]3[C:10]([N:11]=2)=[C:9]([C:12]2[NH:20][C:19]4[C:18]5([CH2:21][CH2:22]5)[CH2:17][NH:16][C:15](=[O:23])[C:14]=4[CH:13]=2)[CH:8]=[CH:7][CH:6]=3)[CH2:27][CH2:26]1Participants
Conditions
- Temperature
- 100 °C
Procedure
Prepared according to Example 131 using 2′-(3-fluoro-2-methyl-5-quinoxalinyl)-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrrolo[3,2-c]pyridin]-4′(1′H)-one (Ex. 77a; 39 mg, 0.12 mmol), cyclopropylamine (Alfa Aesar, Ward Hill, Mass.; 14 mg, 0.25 mmol) and DIPEA (47 mg, 0.36 mmol) and heating at 100° C. for 1 h. Purification by chromatography (silica gel, 0-100% EtOAc in hexanes followed by 0-10% MeOH in DCM) provided 2′-(3-(cyclopropylamino)-2-methyl-5-quinoxalinyl)-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrrolo[3,2-c]pyridin]-4′(1′H)-one (27 mg, 62% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (1H, br s, D2O exch.), 7.95 (1H, dd, J=7.53, 1.47 Hz), 7.58 (1H, dd, J=8.02, 1.37 Hz), 7.42 (1H, dd, J=2.35, 0.59 Hz), 7.36 (1H, br s, D2O exch.), 7.34 (1H, t, J=7.82 Hz), 7.02 (1H, br s, D2O exch.), 3.29 (2H, d, J=2.35 Hz), 2.91 (1H, tq, J=6.75, 3.52 Hz), 2.51 (3H, s), 1.06-1.12 (2H, m), 0.97-1.02 (2H, m), 0.90-0.97 (2H, m), 0.66-0.74 (2H, m). m/z (ESI, +ve) 360.2 (M+H)+.
Workup
- customPrepared
- customPurification by chromatography (silica gel, 0-100% EtOAc in hexanes followed by 0-10% MeOH in DCM)
Sources & evidence
- ORD record
- ord-e6c0c0d8ae774f10b4a5ce2a248577b7
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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