Triethylamine → HCID 86618730, compound

HRID 447661Notes

Reaction equation

HRID 447661 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][C@H:12]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C@@H:22]3[C:30]4[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=4)[C:24]([CH3:33])([CH3:32])[CH2:23]3)[CH:16]=2)[CH2:11][C@H:10]1[CH2:34][OH:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[S:37]([NH2:40])(=[O:39])=[O:38].CCOC(C)=O.CCN(CC)CC>CC(N(C)C)=O.C(#N)C>[S:37](=[O:39])(=[O:38])([O:35][CH2:34][C@@H:10]1[CH2:11][C@@H:12]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C@@H:22]3[C:30]4[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=4)[C:24]([CH3:33])([CH3:32])[CH2:23]3)[CH:16]=2)[CH2:13][C@@H:9]1[O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[NH2:40]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 24499Chlorosulfamic acidHCID 66797923HCID 66797923, compound

Product 1

HCID 86618730HCID 86618730, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of {(1S,2S,4R)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-[(2-{[(1S)-5-chloro-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl]amino}pyridin-4-yl)oxy]cyclopentyl}-methanol (28.1 mg, 0.0000543 mol) in DMA (1.00 mL) was added chlorosulfonamide (0.0251 g, 0.000217 mol) in 0.50 ml acetonitrile. The mixture was stirred for 30 min then poured into 50 ml EtOAc and 1.00 ml Et3N. The layers were separated and the organic layer was washed (water) and concentrated. The residue was purified by preparative plate chromatography (85% EtOAc/hexanes) to afford the title compound (28.7 mg, 89%) as a white solid.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed (water)
  3. concentrationconcentrated
  4. customThe residue was purified by preparative plate chromatography (85% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8a1ee57d693c4f71a010b713b032ead5
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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