HCID 86760559, 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 1180942Notes

Reaction equation

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

Participants

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

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

Sources & evidence

ORD record: ord-ddf2137ed65544e2b852dddbec017c65
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282588B2

Reaction notes

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