Sulfuryl chloride → (R)-N-(4-(5-(3 cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-2-hydroxyacetamide

HRID 1051055Notes

Reaction equation

HRID 1051055 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][C@H:22]4[NH:27][C@H:28](C)[C:29]([O:31]C)=O)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[C@@H]1(N)C2C(=CC=CC=2)CC1.S(Cl)(Cl)(=O)=[O:45]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][C@H:22]4[NH:27][C:28](=[O:45])[CH2:29][OH:31])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:11])[CH3:12])#[N:2]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 70000841-Aminoindane, (S)-HCID 67196373(R)-methyl 2-(((R)-4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)amino)propanoate

Product 1

HCID 58344902(R)-N-(4-(5-(3 cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-2-hydroxyacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)- or (S)-indane amine (1 eq) in DCM (0.05M) was added TEA (2 eq) and the appropriate sulfonyl chloride (2 eq.) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated and the pure product isolated after preparative HPLC purification.

Workup

  1. customat room temperature
  2. customThe solvent was evaporated
  3. customthe pure product isolated
  4. customafter preparative HPLC purification

Sources & evidence

ORD record
ord-705ffdda59d043e39bdd3a7d17f77b40
Source dataset
uspto-grants-2016_07
Patent number
US09388147B2

Reaction notes

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