Hydrochloric Acid → HCID 71253553, compound

HRID 1775114Notes

Reaction equation

HRID 1775114 reaction equation
[CH3:1][C:2]1[C:3]([N:31]2[CH2:35][CH2:34][C@@H:33]([NH:36]C(=O)OC(C)(C)C)[CH2:32]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10](COCC[Si](C)(C)C)[N:9]=2)=[CH:6][CH:7]=1.Cl>CO.O1CCOCC1>[CH3:1][C:2]1[C:3]([N:31]2[CH2:35][CH2:34][C@@H:33]([NH2:36])[CH2:32]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71254231HCID 71254231, compound

Product 1

HCID 71253553HCID 71253553, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To (R)-tert-butyl 1-(3-methyl-6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ylcarbamate in MeOH (4 mL) was added 4.0 M of Hydrogen chloride in 1,4-Dioxane (6 mL). The resulting mixture was stirred overnight at room temperature. The mixture was then concentrated, and the residue was purified by reverse phase HPLC to afford 316 as an off-white solid (15.4 mg, 56.9%). 1H NMR (400 MHz, DMSO) δ 9.27 (d, J=1.7 Hz, 1H), 9.19 (s, 1H), 9.12 (s, 1H), 8.59 (d, J=3.8 Hz, 1H), 8.41 (d, J=8.0 Hz, 1H), 7.53 (dd, J=7.9, 4.8 Hz, 1H), 7.51-7.43 (m, 2H), 3.85 (dd, J=9.5, 5.6 Hz, 2H), 3.77 (dd, J=16.6, 7.1 Hz, 1H), 3.63-3.57 (m, 1H), 3.43 (dd, J=9.6, 5.6 Hz, 1H), 2.37 (s, 3H), 2.11 (td, J=12.2, 5.9 Hz, 1H), 1.74 (dq, J=13.8, 7.1 Hz, 1H); ESI MS m/z=372.2 (M+1)

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c186465725cc4a39bb75d4889ab884aa
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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