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

HRID 79603

Reaction equation

HRID 79603 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-9830e941378f49bfab36fac81c76616d
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Linked notes

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