Methanol → HCID 118365087, compound

HRID 588174Notes

Reaction equation

HRID 588174 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4](C(OCC)=O)[NH:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37].CO>CN(C=O)C>[CH3:39][N:38]([CH3:40])[C:36](=[O:37])[CH2:35][O:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[NH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 118373963HCID 118373963, compound

Product 1

HCID 118365087HCID 118365087, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-Ethyl 3-oxo-6-(3-(1-phenylethyl)ureido)-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate (29 mg, 0.079 mmol), potassium carbonate (32.6 mg, 0.236 mmol), and 2-chloro-N,N-dimethylacetamide (8.8 μL, 0.087 mmol) were stirred in DMF (1 mL) at room temperature for 24 h. MeOH (0.5 mL) was added and the reaction mixture was stirred at room temperature for 1 h. The insoluble inorganics were removed by filtration and the reaction mixture was purified via mass triggered, reverse phase prep-HPLC. Fractions containing pure product were concentrated in vacuo and the residue dissolved in MeOH. The MeOH solution was passed through a PS—HCO3 cartridge and the filtrate concentrated in vacuo to give (R)—N,N-dimethyl-2-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yloxy)acetamide. MS ESI calc'd. For C19H22N6O3 [M+1]+ 383. found 383. 1H NMR (500 MHz, DMSO-d6) δ 11.94 (s, 1H), 8.94 (s, 1H), 8.58 (s, 1H), 7.77 (br s, 1H), 7.49 (s, 1H), 7.34-7.31 (m, 4H), 7.25-7.20 (m, 1H), 5.04 (s, 2H), 4.89-4.83 (m, 1H), 2.98 (s, 3H), 2.82 (s, 3H), 1.39 (d, J=7.0 Hz, 3H).

Workup

  1. customThe insoluble inorganics were removed by filtration
  2. customthe reaction mixture was purified via mass
  3. additionFractions containing pure product
  4. concentrationwere concentrated in vacuo
  5. dissolutionthe residue dissolved in MeOH
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-77e2cfb6f5ff46438f32cc2e342782f8
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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