Methanol → 2-(benzyloxy)-N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide

HRID 79603

반응식

HRID 79603 반응식
ClC1C=CC([C@@H:8]([CH2:32]NC(C)C)[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][CH:24]=[C:25]([NH:26][C:27](=[O:31])[CH2:28]CC)[C:18]=34)[CH2:13][CH2:12]2)=O)=CC=1.C(OCC(O)=O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O=C1N([ClH]P([ClH]N2[CH2:63][CH2:62]OC2=O)=O)CCO1.[CH2:65](N(CC)CC)[CH3:66].C([O-])([O-])=O.[Na+].[Na+].[CH3:78][OH:79]>CN(C=O)C.[Li+].[OH-]>[CH2:78]([O:79][CH2:28][C:27]([NH:26][C:25]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][C:17]=2[N:14]2[CH2:13][CH2:12][N:11]([CH2:9][C:8]3[CH:63]=[CH:62][CH:66]=[CH:65][CH:32]=3)[CH2:16][CH2:15]2)[NH:23][CH:24]=1)=[O:31])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

참가 물질

8

반응물 5

HCID 887MethanolHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 290301(Benzyloxy)acetic acidHCID 44199250(S)-N-(4-(4-(2-(4-chlorophenyl)-3-(isopropylamino)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridin-3-yl)butyramide

생성물 1

HCID 687601872-(benzyloxy)-N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide수율 49.4%

시약·촉매·용매 2

HCID 3939Lithium Hydroxide용매HCID 6228Dimethylformamide용매

실험 절차

4-(4-Benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.30 g, 0.976 mmol, see Example 25), 2-(benzyloxy)acetic acid (0.195 g, 1.17 mmol) and bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP—C1”; 0.298 g, 1.17 mmol) were placed in DMF (3 mL) at room temperature. Triethylamine (0.680 mL, 4.88 mmol) was then added, and the reaction was stirred for 1 hour at room temperature. The reaction was then diluted with MeOH (5 mL), and 3M LiOH (0.5 mL) was added and stirred for 10 minutes. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:10-500:20 DCM:MeOH) to give 2-(benzyloxy)-N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.22 g, 49.4% yield).

후처리

  1. additionwas added
  2. stirringstirred for 10 minutes
  3. extractionextracted into DCM
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude residue that
  8. customwas purified by column chromatography (500:10-500:20 DCM:MeOH)

출처 및 근거

ORD 기록
ord-9830e941378f49bfab36fac81c76616d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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