Hydrochloric Acid → HCID 58382350, compound

HRID 1628079Notes

Reaction equation

HRID 1628079 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13]([C:22]2[N:34]([S:35]([C:38]3[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[C:25]3=[N:26][CH:27]=[C:28]4[CH:32]=[N:31][N:30]([CH3:33])[C:29]4=[C:24]3[CH:23]=2)=[CH:12]1)(C(C)(C)C)(C)C.Cl>CO>[CH3:21][O:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([CH2:10][CH2:9][OH:8])[CH:12]=[C:13]2[C:22]1[N:34]([S:35]([C:38]2[CH:39]=[CH:40][C:41]([CH3:42])=[CH:43][CH:44]=2)(=[O:36])=[O:37])[C:25]2=[N:26][CH:27]=[C:28]3[CH:32]=[N:31][N:30]([CH3:33])[C:29]3=[C:24]2[CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58382240HCID 58382240, compound

Product 1

HCID 58382350HCID 58382350, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-(1-(2-(tert-Butyldimethylsilyloxy)ethyl)-5-methoxy-1H-indol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.130 g, 0.212 mmol, prepared using U from Preparation #P.1.1 with (2-bromoethoxy)(tert-butyl)dimethylsilane) was dissolved in MeOH (5 mL) then HCl (37% aqueous, 0.15 g, 1.3 mmol) was added. The mixture was stirred at rt for about 15 min. The mixture was concentrated under reduced pressure to give 2-(5-methoxy-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)ethanol (0.10 g, 91%): LC/MS (Table 2, Method b) Rt=2.19 min; MS m/z: 516 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-26faf13be85a40ef961bea16de751cad
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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