Dichloromethane → HCID 131729712, compound

HRID 1922313Notes

Reaction equation

HRID 1922313 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[CH3:18][C:19]1[C:24]([CH2:25]O)=[CH:23][CH:22]=[C:21]([CH3:27])[N:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:61]CCl>>[ClH:61].[CH3:18][C:19]1[C:24]([CH2:25][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)=[CH:23][CH:22]=[C:21]([CH3:27])[N:20]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 2784752(2,6-Dimethylpyridin-3-yl)methanolHCID 5363146Diisopropyl azodicarboxylateHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 131729712HCID 131729712, compound

Procedure

A mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (149 mg, 0.583 mmol, Description 3) and (2,6-dimethyl-3-pyridinyl)methanol (80 mg, 0.583 mmol) in dichloromethane (10 ml) was stirred under argon at room temperature. Triphenylphosphine (153 mg, 0.583 mmol) and DIAD (0.113 ml, 0.583 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. Then the reaction mixture was washed with water, dried over sodium sulphate, filtered and evaporated. The desired product was isolated by MDAP, concentrated to a small volume, and partitioned between dichloromethane and aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate, filtered and evaporated in vacuo to afford the desired compound as a free base. This was treated with ethereal hydrochloride/methanol to give the title compound as a white solid (92 mg).

Workup

  1. stirringThe resulting mixture was stirred at room temperature under argon for 16 hours
  2. washThen the reaction mixture was washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-65f03937783b4d7bbb37e686908b55b6
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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