HCID 69000354, compound → 1,1-dimethylethyl (2-{3-(4-{[(dimethylamino)carbonyl]amino}phenyl)-4-[2-(3-formylphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-1-yl}ethyl)methylcarbamate

HRID 28986Notes

Reaction equation

HRID 28986 reaction equation
[CH3:1][N:2]([CH3:45])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][C:24]([C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][OH:33])[CH:27]=5)=[CH:25][C:18]=34)=[CH:15][N:14]([CH2:34][CH2:35][N:36]([CH3:44])[C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[N:13]=2)=[CH:8][CH:7]=1)=[O:4]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:45][N:2]([CH3:1])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][C:24]([C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=[O:33])[CH:27]=5)=[CH:25][C:18]=34)=[CH:15][N:14]([CH2:34][CH2:35][N:36]([CH3:44])[C:37](=[O:43])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42])[N:13]=2)=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 1

HCID 69000354HCID 69000354, compound

Product 1

HCID 866173931,1-dimethylethyl (2-{3-(4-{[(dimethylamino)carbonyl]amino}phenyl)-4-[2-(3-formylphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-1-yl}ethyl)methylcarbamateYield 77.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 1,1-dimethylethyl [2-(3-(4-{[(dimethylamino)carbonyl]amino}phenyl)-4-{2-[3-(hydroxymethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-1-yl)ethyl]methylcarbamate (1.24 g, 2.0 mMol) in CHCl3 (100 mL) was added activated MnO2 (2.5 g, 28.7 mMol). The reaction was stirred and refluxed (70° C. oil bath) for 8 h, cooled to RT, filtered through a pad of Celite®, rinsed with CHCl3, and evaporated to dryness under vacuum. Purification by flash chromatography on silica gel (5 to 10% MeOH in (1:1) EtOAc/CHCl3) provided the title compound (0.94 g, 77%) as a pale yellow solid. ESMS [M+H]+: 608.6.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through a pad of Celite®
  3. washrinsed with CHCl3
  4. customevaporated to dryness under vacuum
  5. customPurification by flash chromatography on silica gel (5 to 10% MeOH in (1:1) EtOAc/CHCl3)

Sources & evidence

ORD record
ord-2fc87909aadc485a83ae6bccb67bfb03
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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