Hydrochloric Acid → HCID 136138789, compound

HRID 2365432Notes

Reaction equation

[ClH:1].[CH2:2]([N:9]([CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)[C:10]1[N:15]=[C:14]2[NH:16][CH:17]=[C:18]([C:19]3[NH:23][N:22]=[CH:21][C:20]=3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:13]2=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>>[ClH:1].[ClH:1].[CH2:2]([N:9]([C:10]1[N:15]=[C:14]2[NH:16][CH:17]=[C:18]([C:19]3[NH:23][N:22]=[CH:21][C:20]=3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:13]2=[CH:12][CH:11]=1)[CH2:30][CH2:31][OH:32])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 136338083HCID 136338083, compound

Product 1

HCID 136138789HCID 136138789, compound

Procedure

The title compound was synthesized by the hydrogen chloride mediated deprotection of N-benzyl-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-3-(4-phenyl-1H-pyrazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine as described in Step 2 of Example 5. Purification by preparative TLC then preparative HPLC, followed by salt formation with 2N HCl/MeOH and final isolation by lyophilization from water afforded 2-{benzyl-[3-(4-phenyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl]-amino}ethanol dihydrochloride in 10% overall yield as a yellow solid.

Workup

customPurification by preparative TLC

Sources & evidence

ORD record: ord-10c3c653341744c19f6d833dfe34686b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697697B2

Reaction notes

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