Phenethylamine → HCID 57810163, 화합물

HRID 1924139노트

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HRID 1924139 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH2:30])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][CH:10]=1.CCN(CC)CC.[C:38]([O:43]CC)(=O)[C:39]([NH2:41])=[O:40].[CH2:46](N)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:38](=[O:43])[C:39]([NH:41][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:40])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 69238Ethyl oxamateHCID 59647511HCID 59647511, 화합물

생성물 1

HCID 57810163HCID 57810163, 화합물수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a 0° C. solution of 3-fluoro-4-[6-methoxy-7-(1-methyl-piperidin-4-ylmethoxy)-quinolin-4-yloxy]-phenylamine (66 mg, 0.13 mmol) and Et3N (0.34 mL) in CH2Cl2 (6 mL) was added slowly ethyl oxalyl chloride (98 mg). The reaction mixture was stirred at rt for 30 min, then diluted with CH2Cl2 and washed with sat. aqueous NaHCO3. After dried over MgSO4 and concentrated, the crude ethyl oxamate was reacted with phenethylamine (80 mg, 0.64 mmol) at 80° C. for 2 h. Purification by HPLC gave product, N-{3-fluoro-4-[6-methoxy-7-(1-methyl-piperidin-4-ylmethoxy)-quinolin-4-yloxy]-phenyl}-N′-phenethyl-oxalamide (52 mg, 68% yield). 1H NMR (400 MHz) δ 9.38 (br s, 1 H), 8.48 (d, J=5.2 Hz, 1 H), 7.83 (dd, J=11.7, 2.6 Hz, 1 H), 7.59 (t, J=6.2 Hz, 1 H), 7.55 (s, 1 H), 7.40-7.20 (8 H), 6.39 (d, J=5.3 Hz, 1 H), 4.06 (d, J=6.6 Hz, 2 H), 4.04 (s, 3 H), 3.67 (q, J=6.8 Hz, 2 H), 2.98 (br d, J=11.5 Hz, 2 H), 2.92 (t, J=7.0 Hz, 2 H), 2.34 (s, 3 H), 2.10-1.80 (m, 5 H), 1.60-1.54 (m, 2 H).

후처리

  1. washwashed with sat. aqueous NaHCO3
  2. dry with materialAfter dried over MgSO4
  3. concentrationconcentrated
  4. customPurification by HPLC

출처 및 근거

ORD 기록
ord-36a0f95e3be5441bb03c8ef005c1b647
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178532B2

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