Trifluoroacetic acid → 4-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}aniline

反応式

[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)OC(C)(C)C)=[CH:18][CH:17]=3)=[CH:12][N:11]=1)[CH2:2]2.FC(F)(F)C(O)=O>>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[CH:12][N:11]=1)[CH2:2]2

参加物

反応物 2

HCID 6422Trifluoroacetic acid

HCID 69430983tert-butyl 4-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}phenylcarbamate

生成物 1

HCID 112201784-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}aniline

実験手順

The product of Example 19B (150 mg, 0.38 mmol) was treated with trifluroacetic acid (2 mL) according to the procedure of Example 18C. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.07) as solid (30 mg, yield, 26%). 1H NMR (300 MHz, MeOH-d4) δ 1.88-2.22 (m, 3H), 2.31-2.45 (m, 1H), 2.56-2.64 (m, 1H), 3.27-3.51 (m, 5H), 3.84-3.96 (m, 1H), 5.36-5.45 (m, 1H), 6.87 (d, J=8.5 Hz, 2H), 7.42 (d, J=8.5 Hz, 2H), 8.77 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+.

後処理

customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.07) as solid (30 mg, yield, 26%)

出典と根拠

ORDレコード: ord-06ba389f300f4e13bebec5c151d23ed9
出典データセット: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07309699B2

反応ノート

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