Methanol → HCID 178527259, compound

HRID 1854488Notes

Reaction equation

HRID 1854488 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3=[C:12]4[CH:18]=[CH:17][NH:16][C:13]4=[N:14][CH:15]=[C:10]3[NH:9][N:8]=2)[CH2:3][CH2:2]1.[CH:19]1([S:22](Cl)(=[O:24])=[O:23])[CH2:21][CH2:20]1.CO>N1C=CC=CC=1>[CH:19]1([S:22]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]3[C:11]4=[C:12]5[CH:18]=[CH:17][NH:16][C:13]5=[N:14][CH:15]=[C:10]4[NH:9][N:8]=3)[CH2:3][CH2:2]2)(=[O:24])=[O:23])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 887MethanolHCID 2760919Cyclopropanesulfonyl chlorideHCID 178419835HCID 178419835, compound

Product 1

HCID 178527259HCID 178527259, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(piperidin-4-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine (0.023 g, 0.095 mmol) in pyridine (0.5 mL) was added cyclopropanesulfonyl chloride (0.015 g, 0.105 mmol). The reaction was stirred at about 25° C. for about 1 h. MeOH (0.5 mL) was added to quench the reaction and the crude reaction mixture was purified by RP-HPLC (Table 2, Method p) to afford 1-(1-(cyclopropylsulfonyl)piperidin-4-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine as a solid (0.004 g, 6.5%): LC/MS (Table 2, Method a) Rt=1.74 min; MS m/z: 346 (M+H)+, 344 (M−H)−.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe crude reaction mixture
  4. customwas purified by RP-HPLC (Table 2, Method p)

Sources & evidence

ORD record
ord-98fb470394c34fe7a02c94a2aad6477a
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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