Chlorosulfonic acid → HCID 86681882, compound

HRID 2409266Notes

Reaction equation

HRID 2409266 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]3[N:15]=[CH:16][CH:17]=[C:13]3[N:12]=[CH:11][C:10]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH3:23])[CH:3]=1.Cl[S:25]([OH:28])(=[O:27])=[O:26]>C(Cl)Cl>[CH2:21]([O:20][C:18]([C:10]1[CH:11]=[N:12][C:13]2[N:14]([N:15]=[CH:16][C:17]=2[S:25]([OH:28])(=[O:27])=[O:26])[C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH3:23])=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 71178932HCID 71178932, compound

Product 1

HCID 86681882HCID 86681882, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 7-(4-fluoro-2-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylate (0.500 g, 1.59 mmol) obtained in step 1 was dissolved in methylene chloride (6 mL), chlorosulfonic acid (0.21 mL, 3.19 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, a 1/1 mixed solvent of diisopropyl ether and 2-propanol was added, and the mixture was stirred at room temperature for 1 hr. The resulting crystals were suction filtered and washed with 2-propanol to give the title compound (0.580 g, 92%). ESI-MS m/z: 395 (M+H)+; 1H-NMR (CDCl3, δ): 1.13 (t, J=7.2 Hz, 3H), 2.29 (s, 3H), 3.94 (q, J=7.2 Hz, 2H), 6.96-7.46 (m, 4H), 8.28 (s, 1H), 8.50 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 1/1 mixed solvent of diisopropyl ether and 2-propanol was added
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. filtrationfiltered
  5. washwashed with 2-propanol

Sources & evidence

ORD record
ord-fd71224099d0437e924ff7c14bac2ff2
Source dataset
uspto-grants-2014_08
Patent number
US08815874B2

Reaction notes

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