1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90039259, compound

HRID 1055395Notes

Reaction equation

HRID 1055395 reaction equation
CCN=C=NCCCN(C)C.[NH2:12][C:13]1[C:18]([O:19][C:20]2([CH:26]([N:30]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:27]([OH:29])=O)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:17]([F:45])[C:16]([F:46])=[CH:15][CH:14]=1>CN(C=O)C.O>[CH2:38]([N:30]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH:26]1[C:20]2([CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[O:19][C:18]2[C:17]([F:45])=[C:16]([F:46])[CH:15]=[CH:14][C:13]=2[NH:12][C:27]1=[O:29])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 90036644HCID 90036644, compound

Product 1

HCID 90039259HCID 90039259, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

H2O (70.5 mg, 460 μmol, Eq: 1.2) and EDCI (88.2 mg, 460 μmol, Eq: 1.2) were added to a solution of [4-(6-amino-2,3-difluoro-phenoxy)-tetrahydro-pyran-4-yl]-dibenzylamino-acetic acid (185 mg, 383 μmol, Eq: 1.00) in DMF (5 mL). The mixture was stirred at RT overnight, diluted with H2O and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography to afford 3-(dibenzylamino)-8,9-difluoro-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-4(5H)-one (102 mg, 57% yield). MS m/z 465.0 (MH+)

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4d9ec141042640c0b5503c848adfa5b0
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…