Pyridine → HCID 178484222, 화합물

HRID 2409815노트

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HRID 2409815 반응식
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[NH:8][N:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:11]=1)=[O:5].N1C=CC=CC=1.[CH3:38][N:39]([CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1)[C:40]([C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45](Cl)=[O:46])=[O:41]>ClCCl.C(OCC)(=O)C>[CH3:38][N:39]([CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1)[C:40](=[O:41])[C:42]1[CH:50]=[CH:49][CH:48]=[C:44]([C:45]([NH:1][C:2]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:22][C:3]=2[C:4](=[O:5])[NH:6][C:7]2[NH:8][N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=3)[N:11]=2)=[O:46])[CH:43]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 867052033-(Methyl(2-morpholinoethyl)carbamoyl)benzoyl chlorideHCID 178507694HCID 178507694, 화합물

생성물 1

HCID 178484222HCID 178484222, 화합물수율 14.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-amino-5-(piperidin-1-yl)-N-(5-(3-(trifluoromethyl)phenyl)-2H-1,2,4-triazol-3-yl)benzamide (50 mg, 0.12 mmol, 1.00 equiv) in dichloromethane (3 mL) was added pyridine (73 mg, 0.92 mmol, 8.00 equiv) followed by the dropwise addition of a solution of 3-(methyl(2-morpholinoethyl)carbamoyl)benzoyl chloride (54 mg, 0.17 mmol, 1.50 equiv) in dichloromethane (2 mL) and the resulting solution was stirred for 30 min at room temperature. The mixture was diluted with 50 mL of ethyl acetate, washed with 2×20 mL of NH4Cl and 2×20 mL of brine, dried over anhydrous sodium sulfate and then concentrated under vacuum. The crude product (50 mg) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 12 mg (10%) of a yellow solid. 1H-NMR (300 MHz, CD3OD, ppm): δ 8.34 (m, 3H), 8.17 (t, J=7.8 Hz, 2H), 7.73 (m, 5H), 7.42 (m, 1H), 3.98 (s, 2H), 3.55 (m, 3H), 3.40 (m, 5H), 3.29 (m, 1H), 3.09 (m, 3H), 1.86 (d, J=4.8 Hz, 4H), 1.71 (t, J=5.1 Hz, 2H). MS (ES, m/z): 705 [M+H]+.

후처리

  1. washwashed with 2×20 mL of NH4Cl and 2×20 mL of brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe crude product (50 mg) was purified by reverse phase HPLC
  5. washeluting with a water/CH3CN gradient
  6. additioncontaining 0.05% TFA

출처 및 근거

ORD 기록
ord-44c9f3b453d14e83af9bd1130cf22931
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815910B2

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