Diisopropylethylamine → HCID 117843009, compound

HRID 2209307Notes

Reaction equation

HRID 2209307 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:27]=1[NH2:28].[C:34]([O:38][C:39]([N:41]1[CH2:44][CH:43]([C:45](O)=[O:46])[CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].CCN(C(C)C)C(C)C>C(#N)C>[Br:25][C:26]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:27]=1[NH:28][C:45]([CH:43]1[CH2:44][N:41]([C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[CH2:42]1)=[O:46]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113102762-Bromo-5-chloroaniline

Product 1

HCID 117843009HCID 117843009, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

HATU (980 mg, 2.58 mmol) was added to a mixture of 2-bromo-5-chloroaniline (352 mg, 1.7 mmol) and 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (402 mg, 2 mmol) in Acetonitrile (8 mL) at room temperature followed by DIPEA (0.74 mL, 4.26 mmol). After stifling overnight, reaction mixture was concentrated under reduced pressure and resulting residue was purified via silica gel column chromatography (0-50% ethyl acetate/hexanes) to yield tert-butyl 3-((2-bromo-5-chlorophenyl)carbamoyl)azetidine-1-carboxylate 7.56 (490 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C15H19BrClN2O3: 389.02; found: 389.57.

Workup

  1. customreaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customresulting residue
  4. customwas purified via silica gel column chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0083b5d2ea194a498574c15e0ee63ab7
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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