HCID 118272430, compound → HCID 118381025, compound

HRID 590799Notes

Reaction equation

HRID 590799 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH:11][C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]2[C:21]([N:24]3[CH2:29][CH2:28][O:27][CH:26]([CH3:30])[CH2:25]3)=[N:22][NH:23][C:17]=2[CH:16]=1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.COC[C@@H](NC(NC1N=CC2C(N3CCO[C@@H](C)C3)=NNC=2C=1)=O)C1C=CC=CC=1>CO>[CH3:1][O:2][CH2:3][C@@H:4]([NH:11][C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]2[C:21]([N:24]3[CH2:29][CH2:28][O:27][C@H:26]([CH3:30])[CH2:25]3)=[N:22][NH:23][C:17]=2[CH:16]=1)=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 118272430HCID 118272430, compoundHCID 118380882HCID 118380882, compound

Product 1

HCID 118381025HCID 118381025, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The enantiomers of 1-((S)-2-Methoxy-1-phenylethyl)-3-(3-(2-methylmorpholino)-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (38 mg, 0.072 mmol) were separated by SFC (Berger Multigram II SFC, column: Chiral Technology IC-H 2.1×25 cm, 5 uM, mobile phase: 39% to 61% MeOH+0.25% dimethyl ethylamine in CO2(1), flow rate: 70 mL/min, 6 min run time). The fractions were collected and the solvent evaporated in vacuo to afford 1-[(1S)-2-methoxy-1-phenylethyl]-3-{3-[(2R)-2-methylmorpholin-4-yl]-1H-pyrazolo[4,3-c]pyridin-6-yl}urea (9.91 mg, 0.024 mmol, 67%) and 1-[(1S)-2-methoxy-1-phenylethyl]-3-{3-[(2S)-2-methylmorpholin-4-yl]-1H-pyrazolo[4,3-c]pyridin-6-yl}urea. MS ESI calc'd. For C21H26N6O3 [M+1]+ 411. found 411. 1H NMR (500 MHz, DMSO-d6) δ 12.01 (s, 1H), 9.09 (s, 1H), 8.82 (s, 1H), 8.09 (br s, 1H), 7.39 (s, 1H), 7.35-7.31 (m, 4H), 7.26-7.21 (m, 1H), 5.00-4.93 (m, 1H), 3.91-3.83 (m, 1H), 3.78 (d, J=12.0 Hz, 1H), 3.74-3.65 (m, 3H), 3.55 (d, J=5.4 Hz, 2H), 3.25 (s, 3H), 2.91-2.82 (m, 1H), 2.59-2.51 (m, 1H), 1.15 (d, J=6.2 Hz, 3H) (Example 39). MS ESI calc'd. For C21H26N6O3 [M+1]+ 411. found 411. 1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 9.35-9.16 (br s, 1H), 9.11 (s, 1H), 8.83 (s, 1H), 8.18-8.09 (br s, 1H), 7.38 (s, 1H), 7.35-7.29 (m, 4H), 7.27-7.20 (m, 8.7, 1H), 5.02-4.90 (m, 1H), 3.93-3.83 (m, 1H), 3.78 (d, J=11.8 Hz, 1H), 3.74-3.64 (m, 3H), 3.55 (d, J=5.4 Hz, 2H), 3.25 (s, 3H), 3.10-3.01 (m, 1H), 2.93-2.82 (m, 1H), 2.60-2.51 (m, 1H), 1.14 (d, J=6.0 Hz, 3H) (Example 40).

Workup

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

Sources & evidence

ORD record
ord-2aa59233fcfd45db82ec440497f610de
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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