Triethylamine → Cyclopropanesulfonic acid N-{1-[6-methoxypyridin-3-yl]-1-[(1-pyridin-2-yl-1H-indazol-5-yl)oxy]propan-2-yl}amide

HRID 1661477Notes

Reaction equation

HRID 1661477 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:18]=[CH:17]3)[CH:10]([NH2:12])[CH3:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:36]1([S:39](Cl)(=[O:41])=[O:40])[CH2:38][CH2:37]1.[NH4+].[Cl-]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:18]=[CH:17]3)[CH:10]([NH:12][S:39]([CH:36]2[CH2:38][CH2:37]2)(=[O:41])=[O:40])[CH3:11])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2760919Cyclopropanesulfonyl chlorideHCID 597865691-[6-Methoxypyridin-3-yl]-1-[1-(pyridin-2-yl)indazol-5-yl]oxypropan-2-amine

Product 1

HCID 24955653Cyclopropanesulfonic acid N-{1-[6-methoxypyridin-3-yl]-1-[(1-pyridin-2-yl-1H-indazol-5-yl)oxy]propan-2-yl}amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[6-methoxypyridin-3-yl]-1-[1-(pyridin-2-yl)indazol-5-yl]oxypropan-2-amine (50 mg, 130 μmol) in dichloromethane (5 mL) was added triethylamine (44 μl), followed by cyclopropane sulfonic acid chloride (28 mg, 200 μmol) and DMAP (1.6 mg, 13 μmol).The stirring was continued for 20 min 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 24 mg as a racemic mixture of two diastereomeres (37%).

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 24 mg as a racemic mixture of two diastereomeres (37%)

Sources & evidence

ORD record
ord-c52e4aeaaf99446c82eba58b57840406
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

Loading…