HCID 70983531, compound → HCID 70982799, compound

HRID 625929Notes

Reaction equation

HRID 625929 reaction equation
[CH2:1]([CH:8]1[C:14]2[CH:15]=[C:16]([O:19][CH2:20][CH2:21][NH:22][S:23]([C:26]3[N:27]=[CH:28][N:29]([CH3:31])[CH:30]=3)(=[O:25])=[O:24])[CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][N:9]1C(OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[K+].C(O)C.[Cl-].[Na+].O>[CH2:1]([CH:8]1[C:14]2[CH:15]=[C:16]([O:19][CH2:20][CH2:21][NH:22][S:23]([C:26]3[N:27]=[CH:28][N:29]([CH3:31])[CH:30]=3)(=[O:25])=[O:24])[CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 70983531HCID 70983531, compound

Product 1

HCID 70982799HCID 70982799, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

0.11 mmol of ethyl 1-benzyl-8-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carboxylate were dissolved in a solution of potassium hydroxide in ethanol (20%). The solution was heated in the microwave at 100° C. for 3 h. The mixture was diluted with brine and extracted with ethyl acetate (3×). The combined organic layers were concentrated in vacuo to give 96 mg of crude material that was purified by flash chromatography to yield 37 mg of N-(2-(1-benzyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (77%).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. concentrationThe combined organic layers were concentrated in vacuo
  3. customto give 96 mg of crude material that
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-a1ac7db9fee84b4dab2b2a218a797f38
Source dataset
uspto-grants-2016_04
Patent number
US09309200B2

Reaction notes

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