Triethylamine → HCID 66681177, compound

HRID 1964664Notes

Reaction equation

HRID 1964664 reaction equation
[OH:1][C@H:2]([CH2:35][OH:36])[CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[N:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N:20]=3)[CH:15]=[C:14]([O:29][C@@H:30]([CH3:34])[CH2:31][O:32][CH3:33])[CH:13]=2)=[CH:10][CH:11]=1)=[O:6].C(N(CC)CC)C.[CH:44]([Si:47](Cl)([CH:51]([CH3:53])[CH3:52])[CH:48]([CH3:50])[CH3:49])([CH3:46])[CH3:45]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[OH:1][C@H:2]([CH2:35][O:36][Si:47]([CH:51]([CH3:53])[CH3:52])([CH:48]([CH3:50])[CH3:49])[CH:44]([CH3:46])[CH3:45])[CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[N:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N:20]=3)[CH:15]=[C:14]([O:29][C@@H:30]([CH3:34])[CH2:31][O:32][CH3:33])[CH:13]=2)=[CH:10][CH:11]=1)=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 66681785HCID 66681785, compound

Product 1

HCID 66681177HCID 66681177, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

N-[(2S)-2,3-Dihydroxypropyl]-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrole-2-carboxamide (666 mg, 1.28 mmol) synthesized in Example (101a) was dissolved in methylene chloride (20 mL), and triethylamine (0.89 mL, 6.40 mmol), triisopropylsilyl chloride (410 μL, 1.92 mmol) and 4-dimethylaminopyridine (234 mg, 1.92 mmol) were added, followed by stirring for 14 hours under nitrogen atmosphere. The reaction solution was diluted with methylene chloride (50 mL), washed with water and saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-60%) to afford the desired product (558 mg, 64%) as a white solid.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialsubsequently dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-60%)

Sources & evidence

ORD record
ord-2c952ea094a0462fa8af9246570e5f65
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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