Dichloromethane → HCID 131729713, compound

HRID 1922314Notes

Reaction equation

HRID 1922314 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.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(Cl)[Cl:60]>>[ClH:60].[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][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:20][CH:19]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 131729713HCID 131729713, compound

Procedure

A mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.392 mmol, Description 3) and 4-pyridinylmethanol (42.7 mg, 0.392 mmol) in DCM (10 ml) were stirred under argon at room temperature. Triphenylphosphine (103 mg, 0.392 mmol) and diisopropyl azodicarboxylate (0.076 ml, 0.392 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. The reaction mixture was washed with water, dried over sodium sulphate, filtered and evaporated. The desired product was isolated by MDAP and concentrated to a small volume. The residual material was partitioned between dichloromethane and aqueous sodium bicarbonate solution, then the organic layer was separated and evaporated. The free base was dissolved in methanol and treated with ethereal hydrochloride to give the title compound as a hydrochloride salt (84 mg).

Workup

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

Sources & evidence

ORD record
ord-3a7a879b3ec6470bae8fa50ae003a406
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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