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Cesium carbonate → HCID 57355799、化合物

HRID 481034
ノート
印刷プレビュー

反応式

HRID 481034 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]2=[O:23])[CH2:10][CH2:9]1)=O)(C)(C)C.Br[CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:25][CH2:26][CH2:27][N:28]3[C:32](=[O:33])[C:31]4=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]4[C:29]3=[O:38])[C:15]2=[O:23])[CH2:12][CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 21611N-3-BromopropylphthalimideHCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

生成物 1

HCID 57355799HCID 57355799、化合物収率 113.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of Compound 9 (42.2 g, 0.13M), prepared in Example 9, and N-(3-bromopropyl)phthalimide (35 g, 0.13M) were dissolved in DMF (300 ml). Cesium carbonate (100 g, 0.3M) was added in one portion and the resulting heterogenous mixture heated in an 80° C. oil bath for 16 hours. The mixture was cooled to room temperature and the DMF removed under reduced pressure. The residue was poured into ice water (800 ml) and stirred at room temperature overnight. The white solid precipitates were collected and dried to give the desired product (60 g, 92%). The BOC group was removed by treatment of a solution of the compound in methylene chloride (500 ml) with excess trifluoroacetic acid (46 ml, 0.6M). The mixture was stirred at room temperature overnight and evaporated to dryness under reduced pressure. The resulting white solids were washed with diethyl ether and dried to give the desired TFA salt. m.p. 173-175° C. 1H NMR (300 MHz, DMSO-d6) δ8.79 (m, 1H; 8.54 (m, 1H); 7.82 (s, 4H); 7.35 (m, 1H); 7.25 (m, 1H); 7.07-6.90 (m, 2H); 4.55 (m, 1H); 3.90 (t, J=7 Hz, 2H); 3.63 (t, J=7 Hz, 2H); 3.42 (m, 2H); 3.15 (m, 2H); 2.60(m, 2H); 2.07 (m, 2H); 1.90 (m, 2H). MS: m/z (MH+) 405

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customthe DMF removed under reduced pressure
  3. additionThe residue was poured into ice water (800 ml)
  4. customThe white solid precipitates
  5. customwere collected
  6. customdried

出典と根拠

ORDレコード
ord-91ff835a0438404e95362b79baa33558
出典データセット
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06653478B2

反応ノート

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