Azetidine → HCID 89582175, compound

HRID 1474708Notes

Reaction equation

HRID 1474708 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.C1C=[C:17]2[N:19]=NN(O)[C:16]2=[CH:15]C=1.O.CCN=C=NCCCN(C)C.Cl.N1CCC1>C(Cl)Cl>[N:19]1([C:10](=[O:12])[CH2:9][C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[F:1])[CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 193619772-Fluoro-4-hydroxyphenylacetic acid

Product 1

HCID 89582175HCID 89582175, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-fluoro-4-hydroxyphenyl)acetic acid (1 g, 5.88 mmol), HOBT monohydrate (2.7 g, 17.6 mmol), and EDC.HCl (3.38 g, 17.6 mmol) were dissolved in 25 mL of DCM and stirred at rt for 30 min. Azetidine (1 g, 17.6 mmol) was added to this mixture and the reaction aged at rt for 3 hrs. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica gel (KP-Sil 50 g SNAP column, Biotage system) eluting with 100% EtOAc over 14 CV to give the desired product. LC/MS (m/z): 210 (M+H)+.

Workup

  1. waitthe reaction aged at rt for 3 hrs
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue purified by column chromatography on silica gel (KP-Sil 50 g SNAP column, Biotage system)
  4. washeluting with 100% EtOAc over 14 CV

Sources & evidence

ORD record
ord-4579b28816e1464897dfdef03eeb534d
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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