Triethylamine → Cyclopropanesulfonic acid N-{1-[2-methoxypyridin-4-yl]-1-[(1-pyridin-3-yl-1H-indazol-5-yl)oxy]propan-2-yl}amide

HRID 1661483Notes

Reaction equation

HRID 1661483 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([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:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[N:18]=[CH:17]3)[CH:10]([NH2:12])[CH3:11])[CH:6]=[CH:5][N: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[CH:8]=[C:7]([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:24]=[N:25][CH:26]=[CH:27][CH:28]=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:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2760919Cyclopropanesulfonyl chlorideHCID 597865661-[2-Methoxypyridin-4-yl]-1-[1-(pyridin-3-yl)indazol-5-yl]oxypropan-2-amine

Product 1

HCID 59786581Cyclopropanesulfonic acid N-{1-[2-methoxypyridin-4-yl]-1-[(1-pyridin-3-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-[2-methoxypyridin-4-yl]-1-[1-(pyridin-3-yl)indazol-5-yl]oxypropan-2-amine (41 mg, 110 μmol) in dichloromethane (4 ml) was added triethylamine (36 μl), followed by cyclopropanesulfonic acid chloride (23 mg, i 60 μmol) and DMAP (1.3 mg, 11 μmol).The stirring was continued for 20 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 4 mg (7.6%) as a racemic mixture of one diastereomer.

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 4 mg (7.6%) as a racemic mixture of one diastereomer

Sources & evidence

ORD record
ord-e40fad2826e64b549655929df9917da6
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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