Triethylamine → HCID 68228670, 화합물

HRID 2370342노트

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HRID 2370342 반응식
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:37])=[C:8]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[C:26]4[C:21](=[C:22]([F:32])[CH:23]=[CH:24][C:25]=4[O:27][C:28]([F:31])([F:30])[F:29])[N:20]([CH2:33][CH2:34][O:35][CH3:36])[CH:19]=3)=[O:17])[CH2:12][CH2:11]2)[CH:9]=1.[NH:38]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:39]([C:43]([NH:45][CH2:46][C:47](O)=[O:48])=[O:44])[CH:40]([CH3:42])[CH3:41].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[C:53]([O:52][C:50](=[O:51])[NH:38][C@H:39]([C:43](=[O:44])[NH:45][CH2:46][C:47](=[O:48])[NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:37])=[C:8]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[C:26]4[C:21](=[C:22]([F:32])[CH:23]=[CH:24][C:25]=4[O:27][C:28]([F:31])([F:29])[F:30])[N:20]([CH2:33][CH2:34][O:35][CH3:36])[CH:19]=3)=[O:17])[CH2:12][CH2:11]2)[CH:9]=1)[CH:40]([CH3:41])[CH3:42])([CH3:54])([CH3:56])[CH3:55]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7014901BOC-VAL-GLY-OHHCID 87328684HCID 87328684, 화합물

생성물 1

HCID 68228670HCID 68228670, 화합물수율 95%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of [4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-[7-fluoro-1-(2-methoxy-ethyl)-4-trifluoromethoxy-1H-indol-3-yl]-methanone hydrochloride (0.3 g, 0.55 mmol), BOC-Val-GlyOH (0.18 g, 0.66 mmol), EDCI (0.126 g, 0.66 mmol), HOBT (0.224 g, 1.65 mmol), and Et3N (0.23 ml, 1.65 mmol) in DMF (15 mL) was stirred at room temperature overnight. The reaction mixture was poured into EtOAc and the organic layer washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give the crude product. Purification by flash chromatography on SiO2 eluting with 3% MeOH/CH2Cl2 provided the desired product (0.4 g, 95%). 1H NMR (300 MHz, CDCl3) δ 7.4 (s, 1H), 7.1 (m, 2H), 7.0-6.8 (m, 3H), 6.7 (bs, 1H), 5.1 (bs, 1H), 4.5-4.3 (m, 4H), 4.1-3.7 (m, 6H), 3.35 (s, 3H), 3.1 (m, 3H), 2.1 (m, 1H), 1.8-1.6 (m, 6H), 1.4 (s, 9H), 0.9 (m, 6H). MS m/z: [M+H]+=768.

후처리

  1. washthe organic layer washed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customPurification by flash chromatography on SiO2 eluting with 3% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-90c331f5bf544b8d937aa05bacdb50c8
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710080B2

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