Bicarbonate Ion → HCID 10115879, compound

HRID 723989Notes

Reaction equation

HRID 723989 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[N:15][N:16]4[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)(O)[O-]>N1C=CC=CC=1.C(OCC)(=O)C>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)=[N:15][N:16]4[CH:21]=[CH:20][C:19]([NH:22][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 31297Methanesulfonyl chlorideHCID 10110826HCID 10110826, compound

Product 1

HCID 10115879HCID 10115879, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-5-amine (60 mg, 0.15 mmol) in anhydrous pyridine (5 mL) was added methylsulfonyl chloride (36 mg, 0.3 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, then saturated aquous bicarbonate was added. The phases were separated, the organic phase was washed with water, brine and dried (magnesium sulfate). Filtration and concentration, followed by flash chromatography (1:1 ethyl acetate-hexane) gave N-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-5-yl]methanesulfonamide (35 mg, 50%) as a solid. 1H-NMR (CDCl3): δ 8.42 (d, 1H), 8.15 (d, 1H), 8.05 (d, 1H), 7.60 (q, 2H), 7.13 (t, 2H), 6.90 (dd, 1H), 6.30 (d, 1H), 5.34 (d, 1H), 4.30 (m, 1H), 3.12 (s, 3H), 1.5–2.2 (m, 8H); 19F-NMR (CDCl3): δ −112.64; MS m/z 467 (M+1).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water, brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ee47b192f7044a6aa1d12ccd91ba9914
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Reaction notes

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