Hydrochloric Acid → HCID 86709783, compound

HRID 1529396Notes

Reaction equation

HRID 1529396 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C1CCCCO1)[N:6]=[C:5]2[C:17]1[N:22]=[C:21]([O:23][C@H:24]2[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28][C:25]32[CH2:27][CH2:26]3)[CH:20]=[N:19][CH:18]=1.[ClH:39]>CC#N>[ClH:39].[ClH:39].[CH2:27]1[C:25]2([CH2:28][CH2:29][NH:30][CH2:31][C@@H:24]2[O:23][C:21]2[N:22]=[C:17]([C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=4)[NH:7][N:6]=3)[CH:18]=[N:19][CH:20]=2)[CH2:26]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67959732HCID 67959732, compound

Product 1

HCID 86709783HCID 86709783, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (4R)-tert-butyl 4-(6-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (314.5 mg, 0.538 mmol) in HCl (5.0M in IPA; 3.0 mL, 15.00 mmol) was stirred under argon at 80° C. for 1 h. The reaction was cooled to RT, diluted with CH3CN (3.0 mL), and vacuum filtered. The collected solid was washed with CH3CN (2×2 mL) and dried in vacuo to provide (R)-3-(6-(6-azaspiro[2.5]octan-4-yloxy)pyrazin-2-yl)-5-bromo-1H-indazole dihydrochloride (256a 205.2 mg, 0.434 mmol, 81% yield) as a yellow solid: MS (ESI, pos. ion) m/z: 400.1/402.1 (M+1).

Workup

  1. filtrationfiltered
  2. washThe collected solid was washed with CH3CN (2×2 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-639bd19c9633452590db9adcbde39ae3
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

Loading…