Hydrochloride methanol → 4-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21166Notes

Reaction equation

N1C2C(=CC=CC=2S([O:14][C:15]2[CH:23]=[CH:22][C:21]([C:24]3[N:25]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:26]4[C:31]([CH:32]=3)=[CH:30][C:29]([CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:28][CH:27]=4)=[C:20]3[C:16]=2[CH2:17][NH:18][C:19]3=[O:47])(=O)=O)C=CC=1.Cl.CO>>[OH:14][C:15]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]([C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[C:26]3[C:31]([CH:32]=2)=[CH:30][C:29]([CH2:33][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:28][CH:27]=3)=[C:20]2[C:16]=1[CH2:17][NH:18][C:19]2=[O:47]

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 866282704-(8-Quinolinesulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneYield 47.9%

Procedure

In a similar manner to Step 2 of Example 233, 4-(8-quinolinesulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0164 g, 0.0251 mmol) was treated with 10% hydrogen chloride-methanol solution (0.650 mL) to obtain Compound 269 (0.00555 g. yield 40%).

Sources & evidence

ORD record: ord-09fe1a5d52814fe5993f4f20ab9aa5a3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Reaction notes

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