Triethylamine → HCID 86618730, compound

HRID 1397597Notes

Reaction equation

HRID 1397597 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-c9f6484f27574b36ae859f4f547ed196
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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