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Cesium carbonate → HCID 49857040, compound

HRID 1466590
Notes
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Reaction equation

HRID 1466590 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[N:21][C:20]=23)=[O:15])[CH:7]=1.I[CH2:28][C:29]1([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]2[C:9]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:10][N:11]([CH2:28][C:29]3([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30]3)[N:12]=2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 136793361-(Iodomethyl)cyclopentan-1-olHCID 66850618HCID 66850618, compound

Product 1

HCID 49857040HCID 49857040, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of N-(5-(5-chloro-2-methoxyphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (prepared as described for Example 14, 115.4 mg, 0.313 mmol) in 3 mL DMF is added 1-(iodomethyl)cyclopentanol (195.4 mg, 2.762 mmol) and cesium carbonate (339.2 mg, 3.327 mmol). The reaction was stirred in a sealed vessel at 140° C. for 18 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic portion washed with brine, dried over magnesium sulfate, and concentrated. The crude product was separated from the other regioisomeric product and purified by reverse phase HPLC and lyophilized to give 32.1 mg (22%) of N-(3-(5-chloro-2-methoxyphenyl)-1-((1-hydroxycyclopentyl)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=467.1; 1H NMR (400 MHz, DMSO-d6) δ: 9.68 (s, 1H), 9.33 (dd, J=7.0, 1.6, 1H), 8.77 (dd, J=4.2, 1.6, 1H), 8.64 (s, 1H), 8.33 (s, 1H), 7.49 (dd, J=8.9, 2.7, 1H), 7.39 (d, J=2.7, 1H), 7.32-7.25 (m, 2H), 4.67 (s, 1H), 4.19 (s, 2H), 3.84 (s, 3H), 1.61 (m, 8H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic portion washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was separated from the other regioisomeric product
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-6f7d442082dc43ddb36e621229ff3a1b
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999998B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes