Triethylamine → HCID 11272324, compound

HRID 2421024Notes

Reaction equation

HRID 2421024 reaction equation
[C:1]1([C:14]([OH:16])=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[CH:3][CH:2]=1.[NH2:17][CH2:18][C@@H:19]([OH:36])[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[CH2:23][CH2:22]1.C(N(CC)CC)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN1CCCC1=O>[Cl:35][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[Cl:34])[O:27][CH:24]1[CH2:23][CH2:22][N:21]([CH2:20][C@H:19]([OH:36])[CH2:18][NH:17][C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]([C:14]([OH:16])=[O:15])=[CH:2][CH:3]=2)=[O:13])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 690651,4-Naphthalenedicarboxylic acidHCID 2733179PyBroPHCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

Product 1

HCID 11272324HCID 11272324, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of naphthalene-1,4-dicarboxylic acid (0.100 g), (2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol (0.147 g) and triethylamine (0.193 mL) in N-methyl-2-pyrolidinone (20 mL) was added PyBrOP (0.258 g). The reaction mixture was stirred for 16 h and the solvent was removed in vacuo. The residue was purified by RPHPLC (Symmetry, 0.1% ammonium acetate/acetonitrile) to afford the title compound as a colourless solid (0.050 g, 20%).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by RPHPLC (Symmetry, 0.1% ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-41018dbce4c54f58ac9a7c312a58a69a
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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