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

HRID 969855

反応式

HRID 969855 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-ef1f0761c06148f982bebc0c262d5757
出典データセット
uspto-grants-2007_12
特許番号
US07307094B2

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