Potassium Carbonate → Methyl {[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}(piperidin-4-yl)acetate

HRID 2093657Notes

Reaction equation

HRID 2093657 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([NH:19][C:20](=[O:41])[C:21]2[CH:26]=[CH:25][C:24]([C:27]3[O:28][C:29]4[C:35]([CH:36]([CH3:38])[CH3:37])=[CH:34][C:33]([C:39]#[N:40])=[CH:32][C:30]=4[N:31]=3)=[CH:23][CH:22]=2)[C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.O.C(=O)([O-])[O-].[K+].[K+]>>[C:39]([C:33]1[CH:34]=[C:35]([CH:36]([CH3:38])[CH3:37])[C:29]2[O:28][C:27]([C:24]3[CH:23]=[CH:22][C:21]([C:20]([NH:19][CH:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[C:15]([O:17][CH3:18])=[O:16])=[O:41])=[CH:26][CH:25]=3)=[N:31][C:30]=2[CH:32]=1)#[N:40]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 22392675Trifluoroacetic acid waterHCID 68744285tert-Butyl-4-(1-{[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}-2-methoxy-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 25169587Methyl {[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}(piperidin-4-yl)acetate

Procedure

To a 40-ml scintillation vial was added tert-butyl-4-(1-{[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}-2-methoxy-2-oxoethyl)piperidine-1-carboxylate (150 mg, 0.268 mmol) and 2 ml of a TFA-water solution [95:5]. The reaction was stirred for 16 h at room temperature and then poured into 5 g of crushed ice and basified with potassium carbonate. The product was extracted with dichloromethane (4×3 ml), and the combined organics were dried (magnesium sulfate), filtered and concentrated in vacuo to provide the title compound as an off-white solid. The crude product was used without further purification in the next step. Mass spectrum (ESI) 461.57 (M+1). 1H NMR (600 MHz, CDCl3): δ8.27 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.92 (d, J=1.1 Hz, 1H), 7.57 (s, 1H), 4.6 (d, J=7.1 Hz, 1H), 3.71 (s, 3H), 3.43 (m, 1H), 3.23 (m, 2H), 2.84 (m, 2H), 2.2 (m, 1H), 1.88 (d, J=13.8 Hz, 2H), 1.51 (m, 2H), 1.40 (d, J=6.8, 6H).

Workup

  1. extractionThe product was extracted with dichloromethane (4×3 ml)
  2. dry with materialthe combined organics were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1af6f79f65a4615a2a13e77c565bf1a
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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