1-Methylpiperazine → HCID 57687046, compound

HRID 908407Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CS(O[CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:21]=[N:22][C:23]([NH2:35])=[C:24]([C:26]3[O:27][C:28]4[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=4[N:30]=3)[CH:25]=2)[CH:17]=[N:16]1)(=O)=O>CN(C=O)C>[O:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[C:24]1[C:23]([NH2:35])=[N:22][CH:21]=[C:20]([C:18]2[CH:17]=[N:16][N:15]([CH2:14][CH2:13][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH:19]=2)[CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-methylpiperazine (0.115 ml) was added to 2-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]ethyl methanesulphonate (138 mg) dissolved DMF (5 ml). The resulting solution was stirred at 100° C. for 1 hour. The mixture was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 2 to 6% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness and the solid was triturated with hot acetonitrile to afford 3-(1,3-benzoxazol-2-yl)-5-[1-[2-(4-methylpiperazin-1-yl)ethyl]pyrazol-4-yl]pyridin-2-amine (109 mg) as a solid. NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 2.30 (bs, 4H), 2.44 (bs, 4H), 2.74 (t, 2H), 4.23 (s, 2H), 7.40-7.50 (m, 2H), 7.65 (bs, 2H), 7.77-7.82 (m, 1H), 7.82-7.87 (m, 1H), 7.90 (s, 1H), 8.24 (s, 1H), 8.40 (d, 1H), 8.51 (d, 1H); Mass spectrum: M+H+ 404.

Workup

custompurified by flash chromatography on silica gel eluting with 2 to 6% methanolic ammonia (7 N) in dichloromethane
customThe solvent was evaporated to dryness
customthe solid was triturated with hot acetonitrile

Sources & evidence

ORD record: ord-e77e09af0ed44e2c91d2e07d6c6aaaf6
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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