1-Methylpiperazine → HCID 178480917, compound

HRID 1695580Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][C:6]1[CH:25]=[CH:24][C:9]2[N:10]=[C:11]([NH:14][C@H:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[O:12][CH2:13][C:8]=2[CH:7]=1)=[O:4].[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(OCC)(=O)C>[C@H:15]1([NH:14][C:11]2[O:12][CH2:13][C:8]3[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:30]4[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]4)[CH:25]=[CH:24][C:9]=3[N:10]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of the above described 2-chloro-N-[2-((R)-indan-1-ylamino)-4H-benzo[d][1,3]oxazin-6-yl]-acetamide (800 mg, 2.248 mmol) and 1-methylpiperazine (5 ml, 45 mmol) was stirred at 23° C. for 18 h. Diluted with ethyl acetate, washed with sat. sodium hydrogen carbonate-solution, dried the organic layer over sodium sulfate. Filtration and removal of the solvent in vacuum left a crude product which was purified by silica gel column chromatography with ethyl acetate to ethyl acetate +10% methanol-ammonium hydroxide (10:1) and trituration with diethyl ether to give the title compound as a white foam (320 mg, 34%), MS (ISP) m/e=420.2 [(M+H)+].

Workup

additionA mixture of the
washwashed with sat. sodium hydrogen carbonate-solution
dry with materialdried the organic layer over sodium sulfate
filtrationFiltration and removal of the solvent in vacuum
waitleft a crude product which
customwas purified by silica gel column chromatography with ethyl acetate to ethyl acetate +10% methanol-ammonium hydroxide (10:1) and trituration with diethyl ether

Sources & evidence

ORD record: ord-558ec917d23840e1b77b75ee31bb6fe1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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