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

HRID 79603

反応式

HRID 79603 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3939Lithium Hydroxide溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9830e941378f49bfab36fac81c76616d
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

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