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Diisopropylethylamine → N-((1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-yl)cyclopropanesulfonamide

HRID 1661475
Notes
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Reaction equation

HRID 1661475 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@@H:11]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[N:20]=[CH:19]4)[C@@H:12]([NH2:14])[CH3:13])[CH:9]=[CH:10][C:2]1=2.CCN(C(C)C)C(C)C.[CH:41]1([S:44](Cl)(=[O:46])=[O:45])[CH2:43][CH2:42]1>CN1C(=O)CCC1.O>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@@H:11]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[N:20]=[CH:19]4)[C@@H:12]([NH:14][S:44]([CH:41]3[CH2:43][CH2:42]3)(=[O:46])=[O:45])[CH3:13])[CH:9]=[CH:10][C:2]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 59339888(1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-amine

Product 1

HCID 59786567N-((1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-yl)cyclopropanesulfonamide

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-amine (43a, 102 mg, 0.24 mmol) and DIPEA (170 μL, 0.97 mmol) was dissolved in NMP (2 mL). cyclopropanesulfonyl chloride (40 μL, 0.39 mmol) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2×10 mL), the organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give an oily residue (NMP residues). The crude material was further purified by HPLC. Yield 80 mg (62%)

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oily residue (NMP residues)
  7. customThe crude material was further purified by HPLC

Sources & evidence

ORD record
ord-3bcbb55fb6c24facb6eab3f2def3d61d
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030340B2

Reaction notes

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