{3-[(Methylcarbamoyl)amino]phenyl}boronic acid → HCID 86588734, compound

HRID 1063918Notes

Reaction equation

HRID 1063918 reaction equation
O1CCCCC1[O:7][NH:8][C:9](=[O:30])[CH2:10][C@@:11]1([C:24]2[S:25][C:26](Br)=[CH:27][CH:28]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:13][CH2:12]1.[CH3:31][NH:32][C:33]([NH:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1)=[O:34]>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:7][NH:8][C:9](=[O:30])[CH2:10][C@@:11]1([C:24]2[S:25][C:26]([C:38]3[CH:39]=[CH:40][CH:41]=[C:36]([NH:35][C:33]([NH:32][CH3:31])=[O:34])[CH:37]=3)=[CH:27][CH:28]=2)[S:17](=[O:18])(=[O:19])[CH2:16][CH2:15][N:14]([S:20]([CH3:23])(=[O:21])=[O:22])[CH2:13][CH2:12]1

Participants

7

Reactant 2

HCID 22276448{3-[(Methylcarbamoyl)amino]phenyl}boronic acidHCID 23402085HCID 23402085, compound

Product 1

HCID 86588734HCID 86588734, compoundYield 13.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(2-tetrahydropyranyloxy)-2-[(S)-7-(5-bromo-2-thienyl)-4-methanesulfonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (230 mg), 3-(methylaminocarbonylamino)phenylboronic acid (123 mg) and tetrakis(triphenylphosphine)palladium(0) (24.4 mg) in a mixture of 1,2-dimethoxyethane (2 ml) and 2M aqueous sodium carbonate solution (0.85 ml) was stirred for 4 hours at 80° C. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The obtained residue was dissolved in methanol (2 ml) and 10% hydrogen chloride in methanol (0.5 ml) was added thereto. After being stirred for 30 minutes at room temperature, the solution was concentrated in vacuo. The residue was purified with silica gel column chromatography (eluent; 0.5-5% methanol in chloroform) to give N-hydroxy-2-[(S)-7-(5-(3-(methylaminocarbonylamino)-phenyl)-2-thienyl)-4-methanesulfonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (30 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with aqueous saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe obtained residue was dissolved in methanol (2 ml)
  6. addition10% hydrogen chloride in methanol (0.5 ml) was added
  7. stirringAfter being stirred for 30 minutes at room temperature
  8. concentrationthe solution was concentrated in vacuo
  9. customThe residue was purified with silica gel column chromatography (eluent; 0.5-5% methanol in chloroform)

Sources & evidence

ORD record
ord-778b49d90fa146b7bd43de5cfeab5e66
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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