(3R)-piperidin-3-ol hydrochloride → HCID 58367182, compound

HRID 1891480Notes

Reaction equation

HRID 1891480 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:14][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][S:28]([CH:31]=[CH2:32])(=[O:30])=[O:29])=[CH:16][N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].Cl.[NH:34]1[CH2:39][CH2:38][CH2:37][C@@H:36]([OH:40])[CH2:35]1>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:14][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][S:28]([CH2:31][CH2:32][N:34]3[CH2:39][CH2:38][CH2:37][C@@H:36]([OH:40])[CH2:35]3)(=[O:30])=[O:29])=[CH:16][N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

4

Reactant 2

HCID 2759333(3R)-piperidin-3-ol hydrochlorideHCID 58367130HCID 58367130, compound

Product 1

HCID 58367182HCID 58367182, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Prepared using General Procedure 13. To a solution of (R)-N-(4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)ethenesulfonamide (10 mg, 0.02 mmol) in DMF (0.5 mL) was added (R)-piperidin-3-ol hydrochloride (20.6 mg, 0.15 mmol) and the reaction was heated to 80° C. for 18 h. The product was purified by preparative HPLC to give 10 mg (80%) of N-((R)-4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)-2-((R)-3-hydroxypiperidin-1-yl)ethanesulfonamide 143. LCMS-ESI (m/z) calculated for C29H34N4O4S2: 566.2; found 567.2 [M+H]+, tR=2.62 min.

Workup

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

Sources & evidence

ORD record
ord-c454856228494cd3918335bb80283371
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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