Methanol → HCID 118272419, compound

HRID 588182Notes

Reaction equation

HRID 588182 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:12][C:13]([NH:15][C:16]2[N:21]=[CH:20][C:19]3[C:22]([O:25][CH3:26])=[N:23][NH:24][C:18]=3[CH:17]=2)=[O:14])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.CO>C(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:12][C:13]([NH:15][C:16]2[N:21]=[CH:20][C:19]3[C:22]([O:25][CH3:26])=[N:23][NH:24][C:18]=3[CH:17]=2)=[O:14])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:12][C:13]([NH:15][C:16]2[N:21]=[CH:20][C:19]3[C:22]([O:25][CH3:26])=[N:23][NH:24][C:18]=3[CH:17]=2)=[O:14])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 118272492HCID 118272492, compound

Product 2

HCID 118272419HCID 118272419, compoundHCID 118365007HCID 118365007, compound

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

The enantiomers of 1-(1-(4-fluorophenyl)-2-methoxyethyl)-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (40 mg, 0.11 mmol) were separated by SFC (Berger Multigram II SFC, column: Phenomenex Lux 4 2.1×25 cm, 5 uM, mobile phase: 30% to 70% MeOH in CO2(l), flow rate: 70 mL/min, 6.5 min run time). The fractions were collected and the solvent evaporated in vacuo to afford 1-[(1R)-1-(4-fluorophenyl)-2-methoxyethyl]-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea and 1-[(1S)-1-(4-fluorophenyl)-2-methoxyethyl]-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea. MS ESI calc'd. For C17H18FN5O3 [M+1]+ 360. found 360. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 9.08 (s, 1H), 8.55 (s, 1H), 7.98 (br s, 1H), 7.47 (s, 1H), 7.36 (dd, J=8.5, 5.5 Hz, 2H), 7.15 (t, J=9.0 Hz, 2H), 4.98-4.92 (m, 1H), 3.96 (s, 3H), 3.55 (d, J=5.0 Hz, 2H), 3.25 (s, 3H) (Example 54). MS ESI calc'd. For C17H18FN5O3 [M+1]+ 360. found 360. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 9.08 (s, 1H), 8.55 (s, 1H), 7.98 (br s, 1H), 7.47 (s, 1H), 7.36 (dd, J=8.5, 5.5 Hz, 2H), 7.15 (t, J=9.0 Hz, 2H), 4.98-4.92 (m, 1H), 3.96 (s, 3H), 3.55 (d, J=5.0 Hz, 2H), 3.25 (s, 3H) (Example 55).

Workup

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

Sources & evidence

ORD record
ord-9b1a7a3d85e24e57ae40949fc86b63bc
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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