Acetic Acid → HCID 123657587, compound

HRID 628428Notes

Reaction equation

HRID 628428 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:54]=[C:55]([Cl:57])[CH:56]=1)[CH2:23][N:24]1[C:32]2[C:27](=[N:28][C:29]([N:33](C(OC(C)(C)C)=O)[NH:34]C(OC(C)(C)C)=O)=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:49]1[CH:53]=[CH:52][NH:51][N:50]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:58](O)(=O)[CH3:59]>>[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:54]=[C:55]([Cl:57])[CH:56]=1)[CH2:23][N:24]1[C:32]2[CH:31]=[CH:30][C:29]3[N:28]([C:58]([CH3:59])=[N:34][N:33]=3)[C:27]=2[CH:26]=[C:25]1[C:49]1[NH:50][N:51]=[CH:52][CH:53]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 178454371HCID 178454371, compound

Product 1

HCID 123657587HCID 123657587, compound

Procedure

A solution of di-tert-butyl 1-[1-[3-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-chlorobenzyl]-2-(1H-pyrazol-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (1.1 g, 1.4 mmol, from Step 3) in acetic acid (28 mL) was heated at 130° C. for 1.5 hours. Acetic acid was removed in vacuo, and the residue was dissolved in DCM and washed with saturated NaHCO3. The aqueous layer was extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-10% MeOH in DCM. Yield: (0.66 g, 54%).

Workup

  1. customAcetic acid was removed in vacuo
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography
  9. washeluting with a gradient from 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-a610e680d4f6474d84b0a08b516cc4c4
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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