Hydrochloric Acid → 1-(7-Amino-5-(3,8-diazabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

HRID 589196Notes

Reaction equation

HRID 589196 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([N:29]2[CH2:35][CH:34]3[N:36](C(OC(C)(C)C)=O)[CH:31]([CH2:32][CH2:33]3)[CH2:30]2)[C:9]=1[C:44]([O:46]CC)=[CH2:45].Cl>O>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([N:29]2[CH2:35][CH:34]3[NH:36][CH:31]([CH2:32][CH2:33]3)[CH2:30]2)[C:9]=1[C:44](=[O:46])[CH3:45]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67295001Tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 672945811-(7-Amino-5-(3,8-diazabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (31 mg) was treated with 4N HCl in H2O (2 mL) and Dixoane (2 mL) until the disappearance of starting material in LCMS. Concentration afforded crude 1-(7-amino-5-(3,8-diazabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone, which was used for next step without further purification, LCMS tR=1.08 Min (10 min run, UV254nm). Mass calculated for, M+H 440.2, observed LC/MS m/z 440.2 (M+H).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-2da378169e7446b5b9a510c2c0a69c57
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

Loading…