Trifluoroacetic acid → HCID 118271826, compound

HRID 588207Notes

Reaction equation

HRID 588207 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:14][C:15]([NH:17][C:18]2[N:23]=[C:22]([CH2:24][OH:25])[C:21]3[C:26]([O:29][CH3:30])=[N:27][NH:28][C:20]=3[CH:19]=2)=[O:16])[C:10]([OH:13])([CH3:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:14][C:15]([NH:17][C:18]2[N:23]=[C:22]([CH2:24][OH:25])[C:21]3[C:26]([O:29][CH3:30])=[N:27][NH:28][C:20]=3[CH:19]=2)=[O:16])[C:10]([OH:13])([CH3:11])[CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118271828HCID 118271828, compound

Product 1

HCID 118271826HCID 118271826, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The enantiomers of 1-(1-(3,4-dichlorophenyl)-2-hydroxy-2-methylpropyl)-3-(4-(hydroxymethyl)-3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea, TFA (15 mg, 0.033 mmol) were separated by SFC (Berger Multigram II, Column: Chiralcel OJ-H, 2.1×25 cm, 5 uM, UV wavelength: 220 nM, mobile phase: 85%/15% Methanol+0.25% dimethyl ethylamine/CO2(l), flow rate: 70 mL/Min, 10 min run time). Elution was observed at 5.8 min. The fractions were collected and the solvent evaporated in vacuo to afford (S)-1-(1-(3,4-dichlorophenyl)-2-hydroxy-2-methylpropyl)-3-(4-(hydroxymethyl)-3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (107, 6.2 mg, 0.014 mmol, 83.0% yield). MS: [M+H]+ m/z 454. 1H NMR (600 MHz, DMSO): 7.51-7.55 (m, 2H); 7.31 (dd, J=8.3, 2.0 Hz, 1H); 7.04 (s, 1H); 4.77 (s, 2H); 4.59 (d, J=8.6 Hz, 1H); 3.94 (s, 3H); 1.16 (s, 6H).

Workup

  1. washElution
  2. customThe fractions were collected
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-fb3d93c344eb4d9bbe22665150021d12
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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