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

HRID 969855

반응식

HRID 969855 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ef1f0761c06148f982bebc0c262d5757
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307094B2

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