Diisopropylethylamine → HCID 67267705, compound

HRID 602100Notes

Reaction equation

HRID 602100 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][C:11](C(O)=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CN([C:20]([O:24]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:50][CH:51]1[CH2:54][N:53]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:52]1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:10][CH:11]=[CH:15][C:16]=2[C:20]([NH:50][CH:51]2[CH2:52][N:53]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:54]2)=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 247299726-(3-Fluorophenyl)nicotinic acid

Product 1

HCID 67267705HCID 67267705, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(3-fluorophenyl)nicotinic acid (0.50 g, 2.30 mmol) in DMF (10 mL) was added HBTU (0.96 g, 2.53 mmol) and DIPEA (0.52 mL, 2.99 mmol). After 1 hr at room temperature, tert-butyl 3-aminoazetidine-1-carboxylate was added and the reaction stirred overnight. The solvent was removed and the residue was partitioned between ethyl acetate and sodium bicarbonate (aqueous saturated). The organic layer was washed with brine (2×), dried (MgSO4), filtered and concentrated to give the desired product, tert-butyl 3-(2-(3-fluorophenyl)nicotinamido)azetidine-1-carboxylate (630 mg, 74%). LC/MS (M+H)=372.2 observed, 372.17 expected

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and sodium bicarbonate (aqueous saturated)
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cff9a86f45a14e37afcb13291f564cc5
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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