Cesium carbonate → HCID 10184334, compound

HRID 861159Notes

Reaction equation

HRID 861159 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:26]4[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=4)=[N:15][N:16]4[C:21]([NH:22][CH:23]5[CH2:25][CH2:24]5)=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][CH:41]1[CH2:43][CH2:42]1>CN(C)C=O>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH2:40][CH:41]5[CH2:43][CH2:42]5)=[CH:30][CH:31]=4)=[N:15][N:16]4[C:21]([NH:22][CH:23]5[CH2:24][CH2:25]5)=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 135433131HCID 135433131, compound

Product 1

HCID 10184334HCID 10184334, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-7-(cyclopropylamino)pyrazolo[1,5-a]pyridin-2-yl]phenol (146 mg, 0.34 mmol) in N,N-dimethylformamide (3 mL) was added cesium carbonate (0.22 g, 0.68 mmol) and (bromomethyl)cyclopropane (66 μL, 0.68 mmol). The reaction was stirred for 1 hour at room temperature, then partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (3:1 to 1:1 hexanes-ethyl acetate) provided 3-[2-(cyclopentylamino)-4-pyrimidinyl]-N-cyclopropyl-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-7-amine (90.4 mg, 55%) as an off-white solid. 1H NMR (CDCl3): δ 7.99 (d, 1 H), 7.84 (d, 1 H), 7.55 (d, 2 H), 7.34 (t, 1 H), 6.98 (d, 2 H), 6.39–6.32 (m, 3 H), 5.08 (broad, 1 H), 4.37 (m, 1 H), 3.87 (d, 2 H), 2.68 (m, 1 H), 2.10 (m, 2 H), 1.80–1.27 (m, 6 H), 0.89 (m, 2 H), 0.78–0.65 (m, 4 H), 0.39 (m, 2 H); MS m/z 481 (M+1).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-cca2063c291d4834946560dd8f57225e
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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