Diisopropylethylamine → HCID 69585863, compound

HRID 1242112Notes

Reaction equation

HRID 1242112 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].[CH:28](N(CC)C(C)C)(C)C.CO[C:39](=[O:52])[C:40]1[CH:45]=[CH:44][C:43](C)=[C:42]([O:47][CH2:48][O:49][CH3:50])[C:41]=1Br>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[CH2:28][C:41]4[C:40](=[CH:45][CH:44]=[CH:43][C:42]=4[O:47][CH2:48][O:49][CH3:50])[C:39]3=[O:52])[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 81531DiisopropylethylamineHCID 59091451HCID 59091451, compoundHCID 69585620HCID 69585620, compound

Product 1

HCID 69585863HCID 69585863, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred mixture of 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 (0.24 g, 0.67 mmol) in acetonitrile (30 ml) was added N,N-diisopropylethylamine (0.16 ml, 0.93 mmol) under nitrogen. 2-Bromo-methyl-3-methoxymethoxy-benzoic acid methyl ester (0.16 g, 0.55 mmol) dissolved in acetonitrile, was added via syringe pump at a rate of 0.3 ml/hour. Once the addition was complete, the reaction mixture was stirred at room temperature for 24 hours. Tlc analysis (1:1 ethyl acetate/hexanes) indicated the reaction to be complete. The volatiles were removed in vacuo and the resultant oil dissolved in ethyl acetate/water. The layers were separated and the aqueous layer extracted with ethyl acetate (3×). The organic layers were combined, dried (MgSO4), filtered and the solvebt evaporated in vacuo, which afforded 0.34 g (100%) of 2-amino-5-(S)-(4-methoxymethoxy-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-6-(1-(S)-phenyl-ethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester, which was used without further purification in the next step.

Workup

  1. additionwas added via syringe pump at a rate of 0.3 ml/hour
  2. additionOnce the addition
  3. customthe reaction
  4. customThe volatiles were removed in vacuo
  5. dissolutionthe resultant oil dissolved in ethyl acetate/water
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with ethyl acetate (3×)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvebt evaporated in vacuo, which

Sources & evidence

ORD record
ord-61292548ceeb4aa39cff7c48cb33f593
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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