Hydrochloric Acid → N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide Hydrochloride

HRID 506267ノート

反応式

HRID 506267 の反応式
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][CH:5]([NH:11][C:12]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[N:20][C:19]=13)=[O:13])[CH2:6]2.[ClH:30]>CO.C(OCC)C>[ClH:30].[CH3:1][N:2]1[CH:3]2[CH2:10][CH2:9][CH2:8][CH:7]1[CH2:6][CH:5]([NH:11][C:12]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[N:20][C:19]=13)=[O:13])[CH2:4]2

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 136162984N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide

生成物 1

HCID 136344233N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide Hydrochloride収率 54%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide (66 mg, 0.17 mmol) in methanol (1.0 mL) was added a solution of HCl in diethyl ether (1 N, 0.18 mL, 0.18 mmol) at room temperature slowly. The reaction mixture was diluted with diethyl ether. The resulting solid was filtered and washed with diethyl ether to afford N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide hydrochloride (39 mg, 54%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 12.30 (br s, 0.5H), 12.01 (br s, 0.5H), 8.30-8.10 (m, 2H), 7.90-7.75 (m, 1H), 7.58-7.50 (m, 2H), 7.18-7.12 (m, 2H), 4.95-4.85 (m, 0.5H), 4.70-4.60 (m, 0.5H), 3.70-3.55 (m, 2H), 3.25-3.15 (m, 1H), 3.00-2.75 (m, 5H), 2.50-2.00 (m, 5H), 1.90-1.50 (m, 4H); MS (ESI+) m/z 392 (M+H); HPLC 96.7% (AUC), tR=12.44 min.

後処理

  1. filtrationThe resulting solid was filtered
  2. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-ea4de87a79684b1f9872b2404ed4df46
出典データセット
uspto-grants-2010_08
特許番号
US07781430B2

反応ノート

読み込み中…