Hydrochloric Acid → HCID 22010748, 화합물

HRID 323175노트

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HRID 323175 반응식
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:50]=[CH:49][C:20]([C:21]([N:23]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=4[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([N:40]4[CH2:45][CH2:44][CH:43]([N:46]([CH3:48])[CH3:47])[CH2:42][CH2:41]4)=[O:39])[CH3:24])=[O:22])=[CH:19][C:18]=3[O:51][CH3:52])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH2:53]=O.[C:55]([BH3-])#[N:56].[Na+].[ClH:59]>CO.C(O)(=O)C.C(O)C>[ClH:59].[ClH:59].[CH3:53][N:56]([CH3:55])[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:50]=[CH:49][C:20]([C:21]([N:23]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=4[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([N:40]4[CH2:45][CH2:44][CH:43]([N:46]([CH3:48])[CH3:47])[CH2:42][CH2:41]4)=[O:39])[CH3:24])=[O:22])=[CH:19][C:18]=3[O:51][CH3:52])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22010797HCID 22010797, 화합물

생성물 1

HCID 22010748HCID 22010748, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

To a solution of 4-(4′-aminobiphenyl-2-carboxamido)-3-methoxy-N-[2-[5-(4-dimethylaminopiperidin-1-ylcarbonyl)pent-1-yloxy]-4-methylphenyl]-N-methylbenzamide (180 mg) and 37% formalin (3 ml) in methanol (20 ml) and acetic acid (0.5 ml) was added sodium cyanoborohydride (80 mg) at ambient temperature. The mixture was stirred at same temperature for 3 hours and quenched with saturated sodium hydrogen carbonate. The mixture was extracted with ethyl acetate and washed with saturated sodium hydrogen carbonate, brine and dried over sodium sulfate. The solvent was removed by evaporation and the crude product was purified by preparative thin layer chromatography (10% methanol in chloroform) to give free product. To a solution of this product (120 mg) in ethanol (10 ml) was added 1N hydrochloric acid (0.33 ml) and stirred at ambient temperature for 10 minutes. The solvent was removed to give 4-(4′-dimethylaminobiphenyl-2-carboxamido)-3-methoxy-N-[2-[5-(4-dimethylaminopiperidin-1-ylcarbonyl)pent-1-yloxy]-4-methylphenyl]-N-methylbenzamide dihydrochloride (130 mg) as amorphous.

후처리

  1. customquenched with saturated sodium hydrogen carbonate
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe crude product was purified by preparative thin layer chromatography (10% methanol in chloroform)
  7. customto give free product
  8. stirringstirred at ambient temperature for 10 minutes
  9. customThe solvent was removed

출처 및 근거

ORD 기록
ord-1ae49a2af40d4f6d8b1fd76f77dc3aa1
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211242B1

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