Triethylamine → HCID 87801558, compound

HRID 852256Notes

Reaction equation

HRID 852256 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH2:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[C:20]([Cl:21])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:22])=[O:14])=[CH:8][CH:7]=1.[C:25]([N:32]1[CH:36]=[CH:35]N=[CH:33]1)(N1C=CN=C1)=[S:26].C(N([CH2:42][CH3:43])CC)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:23][C:25]([N:32]([C:36]1[CH:35]=[CH:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:43]1[CH:42]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:33])=[S:26])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([C:15]2[C:16]([Cl:22])=[CH:17][N:18]=[CH:19][C:20]=2[Cl:21])=[O:14])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 58724387HCID 58724387, compound

Product 1

HCID 87801558HCID 87801558, compoundYield 122.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-Amino-3-{4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl}propionic acid methyl ester (0.25 g, 0.62 mmol) was added at room temperature to a tetrahydrofuran solution (3 ml) of thiocarbonyidiimidazol (0.12, 0.68 mmol) and triethylamine (0.062, 0.62 mmol) and stirred for 2 h. Next, the solvent was removed under reduced pressure and compound from Preparation 11 was added in acetonitrile (3 ml) and stirred at 80° C. for 3 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (Hexane:AcOEt, 1:1) to yield the title compound(0.23 g, 62%) as a yellow solid.

Workup

  1. customNext, the solvent was removed under reduced pressure and compound from Preparation 11
  2. additionwas added in acetonitrile (3 ml)
  3. stirringstirred at 80° C. for 3 h
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (Hexane:AcOEt, 1:1)

Sources & evidence

ORD record
ord-0032a1199cf04046a2caf9f4c380aabe
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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