Triethylamine → HCID 10187558, compound

HRID 229831Notes

Reaction equation

HRID 229831 reaction equation
[CH3:1][CH:2]([CH3:39])[CH2:3][C@H:4]([NH:26][C:27]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:28])[C:5](=[O:25])[NH:6][C@H:7]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[N:10]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)(=[O:17])=[O:16])[CH2:9][CH:8]1[OH:24].C(N(CC)CC)C>CS(C)=O.O>[CH3:1][CH:2]([CH3:39])[CH2:3][C@H:4]([NH:26][C:27]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:28])[C:5](=[O:25])[NH:6][C@H:7]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[N:10]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)(=[O:17])=[O:16])[CH2:9][C:8]1=[O:24]

Participants

5

Reactant 2

HCID 8471Triethylamine2×HCID 86591324HCID 86591324, compound

Product 1

HCID 10187558HCID 10187558, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sulfur trioxide-pyridine complex (11 mg, 0.7 mmol) was added to a solution of quinoline-6-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-hydroxy-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide (130 mg, 0.235 mmol) in DMSO (2.0 ml) and triethylamine (0.2 ml, 1.4 mmol) was stirred at RT for 1 h. The reaction was incomplete; therefore, additional triethyl amine (0.2 ml, 1.4 mmol) and sulfur trioxide-pyridine complex (11 mg, 0.7 mmol) was added and the reaction was stirred an additional hour. The reaction mixture was diluted with water, then was extracted with EtOAc. Then, the organic layer was was extracted with brine. The combined organics were dried with magnesium sulfate, filtered, concentrated in vacuo, and purified by column chromatography (3% MeOH/CH2Cl2) gave the title compound (100 mg, 77%): 1H NMR:9.0 (sm 1H), 8.70 (s, 1H), 7.90-8.30 (m, 6H), 7.50-7.55 (m, 2H), 7.10 (d, 1H), 7.0 (d, 1H), 5.10-5.15 (m, 1H), 4.70-4.80 (m, 2H), 4.35-4.40 (m, 1H), 3.85 (d, 1H), 2.0-2.25 (m, 3H), 1.70-1.80 (m, 2H), 1.60-1.70 (m, 2H), 0.90-1.10 (m, 9H); Electrospray mass spec: M+H+=552.4

Workup

  1. stirringthe reaction was stirred an additional hour
  2. extractionwas extracted with EtOAc
  3. extractionThen, the organic layer was was extracted with brine
  4. dry with materialThe combined organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ec85f8a59623446aba93b31de7fcc80b
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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