Water → HCID 59296048, compound

HRID 2233416Notes

Reaction equation

HRID 2233416 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:17]([OH:19])=O)=[CH:11][NH:12][C:13]2=[O:16])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:32][CH2:33][C@@H:34]([OH:51])[CH2:35][N:36]1[CH2:41][CH2:40][CH:39]([O:42][C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([Cl:50])[CH:44]=2)[CH2:38][CH2:37]1.O>CN(C)C=O>[Cl:50][C:45]1[CH:44]=[C:43]([CH:48]=[CH:47][C:46]=1[Cl:49])[O:42][CH:39]1[CH2:38][CH2:37][N:36]([CH2:35][C@H:34]([OH:51])[CH2:33][NH:32][C:17]([C:10]2[C:9]3[C:14](=[CH:15][C:6]([S:3]([NH:2][CH3:1])(=[O:4])=[O:5])=[CH:7][CH:8]=3)[C:13](=[O:16])[NH:12][CH:11]=2)=[O:19])[CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-olHCID 59295967HCID 59295967, compound

Product 1

HCID 59296048HCID 59296048, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7-[(Methylamino)sulfonyl]-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid (0.1 g) in dimethyl formamide (7 ml) was treated with N,N-carbonyldiimidazole (0.06 g) and the mixture was heated at 55° C. for 45 min. (2R)-1-Amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol (0.11 g) in dimethyl formamide (1 ml) was added and the mixture was stirred at ambient temperature for 18 h. 1 Drop of water was added and the solvent was evaporated. Purification using revere phase HPLC (Symmetry C8 column) and acetonitrile/aqueous ammonium acetate as eluent yielded the title compound as a white solid (0.03 g).

Workup

  1. additionwas added
  2. customthe solvent was evaporated
  3. customPurification

Sources & evidence

ORD record
ord-4be604ca53c64899aa6add1d61e046b6
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

Loading…