Triethylamine → HCID 86633466, compound

HRID 1672163Notes

Reaction equation

HRID 1672163 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3([CH2:15][OH:16])[CH2:14][CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.CCN(CC)CC.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3([CH2:15][O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:14][CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67336208HCID 67336208, compound

Product 1

HCID 86633466HCID 86633466, compoundYield 139.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of [1-(1H-indazol-5-ylamino)-cyclobutyl]-methanol (0.690 g, 3.18 mmol) in DCM (100 mL) at ambient temperature and under nitrogen was added Et3N (2.66 mL, 19.1 mmol) followed by methanesulfonyl chloride (0.74 mL, 9.54 mmol). After 5 minutes the mixture was washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4), filtered and concentrated in vacuo to give methanesulfonic acid 1-(1H-indazol-5-ylamino)-cyclobutylmethyl ester (1.31 g) as a gum that was used directly in the next step without further purification.

Workup

  1. washAfter 5 minutes the mixture was washed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-367cfbf1b9b34a85a0e5914cfe38843f
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

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