HCID 11173633, compound → cis-1-[4-(6-Acetamido-2-methylpyridin-3-yl)benzoyl]-6-(3,5-dimethylpiperazin-1-yl)-5-methoxyindoline

HRID 2214758Notes

Reaction equation

[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][CH2:14][NH:15]3)=[CH:11][C:10]=2[O:18][CH3:19])[CH2:3]1.C[Al](C)C.[C:24]([NH:27][C:28]1[N:33]=[C:32]([CH3:34])[C:31]([C:35]2[CH:44]=[CH:43][C:38]([C:39](OC)=[O:40])=[CH:37][CH:36]=2)=[CH:30][CH:29]=1)(=[O:26])[CH3:25]>C1(C)C=CC=CC=1>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][CH2:14][N:15]3[C:39]([C:38]3[CH:37]=[CH:36][C:35]([C:31]4[CH:30]=[CH:29][C:28]([NH:27][C:24](=[O:26])[CH3:25])=[N:33][C:32]=4[CH3:34])=[CH:44][CH:43]=3)=[O:40])=[CH:11][C:10]=2[O:18][CH3:19])[CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred solution of D3 (40 mg, 150 umole) in toluene (2 ml) at room temperature under argon was treated with 2M trimethylaluminium in toluene (0.15 ml, 300 umole) and maintained for 15 min, then a solution of D7 (57 mg, 200 umole) in toluene (3 ml) was added and the mixture heated at 90° C. for 1 h. The solution was allowed to cool, then added directly to a silica gel column (5 g) and eluted initially with 2% MeOH/DCM to remove high Rf impurities, then with 10% MeOH/DCM to afford the product. This was triturated with Et2O/DCM to afford the title compound as a beige solid (35 mg, 82%).

Workup

temperaturemaintained for 15 min
temperatureto cool
additionadded directly to a silica gel column (5 g)
washeluted initially with 2% MeOH/DCM
customto remove high Rf impurities
customwith 10% MeOH/DCM to afford the product
customThis was triturated with Et2O/DCM

Sources & evidence

ORD record: ord-070a8aed011e44258801dc36598743b2
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109201B2

Reaction notes

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