(R)-3-Pyrrolidinol → HCID 58367352, compound

HRID 1891479Notes

Reaction equation

HRID 1891479 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([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][S:28]([CH:31]=[CH2:32])(=[O:30])=[O:29])=[N:15][N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[NH:33]1[CH2:37][CH2:36][C@@H:35]([OH:38])[CH2:34]1>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([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][S:28]([CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][C@@H:35]([OH:38])[CH2:34]3)(=[O:29])=[O:30])=[N:15][N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

4

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 58367160HCID 58367160, compound

Product 1

HCID 58367352HCID 58367352, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Prepared using General Procedure 13. To a solution of (S)-N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)ethenesulfonamide (40 mg, 0.5 mmol) in DMF (0.5 mL) was added (R)-pyrrolidin-3-ol (18.7 mg, 0.21 mmol) and the reaction was heated to 80° C. for 18 h. The product was purified by preparative HPLC to give 30 mg (56%) of N-((S)-4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2-((R)-3-hydroxypyrrolidin-1-yl)ethanesulfonamide 37 as an off-white solid. LCMS-ESI (m/z) calculated for C27H31N5O4S2: 553.2; found 554.2 [M+H]+, tR=2.52 min.

Workup

  1. customPrepared
  2. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-d6f5892b121a432783f2149d1f6b8b7e
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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