Triethylamine → Cyclopropanesulfonic acid N-{1-[2-methoxypyridin-4-yl]-1-[(1-pyridin-2-yl-1H-indazol-5-yl)oxy]butan-2-yl}amide

HRID 1661485Notes

Reaction equation

HRID 1661485 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:19]=[CH:18]3)[CH:10]([NH2:13])[CH2:11][CH3:12])[CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[CH:37]1([S:40](Cl)(=[O:42])=[O:41])[CH2:39][CH2:38]1.[NH4+].[Cl-]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:19]=[CH:18]3)[CH:10]([NH:13][S:40]([CH:37]2[CH2:39][CH2:38]2)(=[O:42])=[O:41])[CH2:11][CH3:12])[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2760919Cyclopropanesulfonyl chlorideHCID 597865651-[2-methoxypyridin-4-yl]-1-[(1-pyridin-2-yl-1H-indazol-5-yl)oxy]butan-2-amine

Product 1

HCID 24955656Cyclopropanesulfonic acid N-{1-[2-methoxypyridin-4-yl]-1-[(1-pyridin-2-yl-1H-indazol-5-yl)oxy]butan-2-yl}amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[2-methoxypyridin-4-yl]-1-[(1-pyridin-2-yl-1H-indazol-5-yl)oxy]butan-2-amine (122 mg, 310 μmol) in dichloromethane (11 ml) was added triethylamine (100 μl), followed by cyclopropanesulphonic acid chloride (66 mg, 470 μmol) and DMAP (3.8 mg, 31 μmol). The stirring was continued for 48 h at room temp. The reaction mixture was poured into sat. NH4Cl solution and extracted with dichloromethane then the solvent was removed i.vac., and the product purified by chromatography on silica gel. Yield 10 mg (6.5%) as a racemic mixture of two diastereomeres.

Workup

  1. extractionextracted with dichloromethane
  2. customthe solvent was removed i.vac
  3. custom, and the product purified by chromatography on silica gel
  4. additionYield 10 mg (6.5%) as a racemic mixture of two diastereomeres

Sources & evidence

ORD record
ord-124558f22e014df8b9917151d91cc593
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

Loading…