Water → HCID 90037478, compound

HRID 1055388Notes

Reaction equation

HRID 1055388 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][C:5]1([CH:11]([N:15]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](O)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[CH2:23]([N:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][C:3]2[CH:30]=[CH:31][CH:32]=[CH:33][C:2]=2[NH:1][C:12]1=[O:13])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 90036487HCID 90036487, compound

Product 1

HCID 90037478HCID 90037478, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(1-(2-Aminophenoxyl)cyclohexyl)-2-(dibenzylamino)acetic acid (0.6365 g, 1.43 mmol, Eq: 1.00), HOBT.H2O (307 mg, 2.00 mmol, Eq: 1.4) and EDCI (274 mg, 1.43 mmol, Eq: 1.00) in DMF (12 mL) were stirred at RT for 1 h and the mixture was diluted with EtOAc. The mixture was washed with sat. NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography to afford 3-(dibenzylamino)-3H-spiro[benzo[b][1,4]oxazepine-2,1′-cyclohexan]-4 (5H)-one as an off-white solid (0.387 g, 64%). MS m/z 427.1 (MH+)

Workup

  1. washThe mixture was washed with sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9bfac5d291b54ebeb2a9f016ee554eea
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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