Water → methanesulfonic acid 2-methyl-3-[4-(7-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrazolo[1,5-a]pyridin-5-ylmethyl ester

HRID 216652Notes

Reaction equation

HRID 216652 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].O[CH2:11][C:12]1[CH:17]=[CH:16][N:15]2[N:18]=[C:19]([CH3:38])[C:20]([C:21]3[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=3[C:26]3[C:34]4[C:29](=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=4)[NH:28][CH:27]=3)=[C:14]2[CH:13]=1.C(N(CC)CC)C.O>C1COCC1>[CH3:38][C:19]1[C:20]([C:21]2[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=2[C:26]2[C:34]3[C:29](=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)=[C:14]2[CH:13]=[C:12]([CH2:11][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=[CH:16][N:15]2[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 591920083-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

Product 1

HCID 59192039methanesulfonic acid 2-methyl-3-[4-(7-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrazolo[1,5-a]pyridin-5-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonic anhydride (815 mg, 4.49 mmol, 4.3 equiv) is added at room temperature under an atmosphere of argon to a solution of 3-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (400 mg, 1.04 mmol) and of triethyl amine (0.314 ml, 2.25 mmol, 2.2 equiv) in anhydrous THF (10 ml). The reaction mixture is stirred for 1 hour at room temperature. Water is added, and the mixture is extracted three times with EtOAc. The combined organic layers are dried over Na2SO4, filtered, and concentrated in vacuo. The residue (450 mg, 94%) is used directly in the next transformation.

Workup

  1. extractionthe mixture is extracted three times with EtOAc
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4a8f05e9c0946b985f74cf4cf036ac5
Source dataset
uspto-grants-2012_06
Patent number
US08193236B2

Reaction notes

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