Triethylamine → HCID 69585712, compound

HRID 1242109Notes

Reaction equation

HRID 1242109 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([CH2:17][NH2:18])[N:13]([C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C[O:36][C:37](=O)[C:38]1[C:43]([O:44][CH3:45])=[CH:42][CH:41]=[CH:40][C:39]=1[CH2:46]Cl>C(#N)C>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([CH2:17][N:18]3[CH2:46][C:39]4[C:38](=[C:43]([O:44][CH3:45])[CH:42]=[CH:41][CH:40]=4)[C:37]3=[O:36])[N:13]([C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11687155HCID 11687155, compoundHCID 59091451HCID 59091451, compound

Product 1

HCID 69585712HCID 69585712, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Amino-5-(S)-aminomethyl-6-(1-(S)-phenyl-ethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (0.55 g, 1.42 mmol) and triethylamine (396 μl, 2.84 mmol) was heated in acetonitrile (15 ml) under an atmosphere of nitrogen to 60° C. whereupon a solution of 2-chloromethyl-6-methoxy-benzoic acid methyl ester (0.32 g, 1.49 mmol) in acetonitrile (5 ml) was added dropwise over the course of 3 hours, keeping the reaction mixture at 60° C. The reaction was allowed to cool to room temperature and was left for 16 hours before the solvent was evaporated in vacuo. The product was purified by column chromatography (SiO2, Flash 40, ethyl acetate-petrol ether) to give 400 mg (53%) of 2-amino-5-(S)-(7-methoxy-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-6-((S)-1-phenyl-ethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil.

Workup

  1. additionwas added dropwise over the course of 3 hours
  2. customat 60° C
  3. customwas evaporated in vacuo
  4. customThe product was purified by column chromatography (SiO2, Flash 40, ethyl acetate-petrol ether)

Sources & evidence

ORD record
ord-59be4e00900b4a93952bd7f3ffd7a246
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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