Triethylamine → HCID 59025498, compound

HRID 1444837Notes

Reaction equation

HRID 1444837 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:14][N:13]([CH2:15][C:16](O)=[O:17])[C:12](=[O:19])[CH:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:10]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:9]1=2.[NH:29]1[CH2:34][CH2:33][CH:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30]1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:9]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:10]=2[CH:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:12](=[O:19])[N:13]([CH2:15][C:16]([N:29]2[CH2:34][CH2:33][CH:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30]2)=[O:17])[CH2:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 76257Diethyl cyanophosphonateHCID 59025465[5-(2-Bromophenyl)-7-chloro-1-isobutyl-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]acetic acid

Product 1

HCID 59025498HCID 59025498, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

190 mg of the compound from Example 6 (0.39 mol) and 65 mg of ethyl piperidine-4-carboxylate (0.41 mol) are dissolved in 5.0 ml of dimethylformamide, and 75 mg of diethyl cyanophosphonate (0.43 mol) and 81 μl of triethylamine (59 mg, 0.58 mol) are added. The reaction mixture is stirred at room temperature for 2.5 h, then mixed with ethyl acetate and washed with 5% strength potassium bisulphate solution, saturated sodium bicarbonate solution and saturated sodium chloride. The organic phase is dried over sodium sulphate, the solvent is removed in a rotary evaporator, and the residue is purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→95:5). 204 mg (87% of theory) of the title compound are obtained.

Workup

  1. washwashed with 5% strength potassium bisulphate solution, saturated sodium bicarbonate solution and saturated sodium chloride
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customthe solvent is removed in a rotary evaporator
  4. customthe residue is purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-34795e2c416f4f258c0c9e6f3f530d2c
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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