Sodium Bicarbonate → HCID 86652268, compound

HRID 1256286Notes

Reaction equation

HRID 1256286 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=1.[N:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:21][CH:20]2[C:22](Cl)=[O:23])=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:22]([C@@H:20]2[CH2:21][C@H:19]2[C:16]2[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=2)=[O:23])[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amineHCID 767027172-(Pyridin-4-yl)cyclopropanecarbonyl chloride

Product 1

HCID 86652268HCID 86652268, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

In a 100 mL round-bottomed flask was added 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 2.74 g, 15.02 mmol) in pyridine (75 ml) to give a yellow solution. Then, at 0° C., 2-(pyridin-4-yl)cyclopropanecarbonyl chloride (7D, 0.19 g, 1.046 mmol) in pyridine (1 ml) was added to give a suspension. After the reaction was complete, saturated NaHCO3 solution was added and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica using 20% MeOH/CH2Cl2 to provide trans-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide (7E, 213 mg, 4% for 3 steps) as a yellow solid. 1H NMR (DMSO-d6) δ: 11.43 (s, 1H), 8.46 (d, J=6.1 Hz, 2H), 7.97 (s, 1H), 7.15-7.27 (m, 2H), 6.40 (s, 1H), 2.39-2.46 (m, 4H), 2.28-2.35 (m, 1H), 1.46-1.67 (m, 2H). ESI-MS: m/z 328.0 (M+H)+.

Workup

  1. customto give a yellow solution
  2. customto give a suspension
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica using 20% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-f973b237c91845e88ba26719d4125a06
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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