Potassium Carbonate → HCID 58928995, compound

HRID 853669Notes

Reaction equation

HRID 853669 reaction equation
C(OC(=O)[O:5][C:6]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:14](=[O:27])[C:13]=2[C:12]([O:28][CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:11]2[C:7]=1[N:8]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH:9]=[N:10]2)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C1C=CN=CC=1)C.O>[CH:29]([O:28][C:12]1[C:13]2[C:14](=[O:27])[N:15]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[C:16](=[O:18])[C:17]=2[C:6]([OH:5])=[C:7]2[C:11]=1[N:10]=[CH:9][N:8]2[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 58928833HCID 58928833, compound

Product 1

HCID 58928995HCID 58928995, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Carbonic acid 8-benzhydryloxy-3-benzyl-6-(4-fluoro-benzyl)-5,7-dioxo-3,5,6,7-tetrahydro-1,3,6-triaza-s-indacen-4-yl ester ethyl ester 257 (130 mg, 0.20 mmol) was dissolved in THF (5 mL, 0.1 M) along with DMAP (24 mg, 0.40 mmol, 2 equiv.). A solution of K2CO3 (276 mg, 1.99 mmol, 10 equiv.) was dissolved separately in H2O (6 mL) before transferring to the reaction mixture. The reaction was allowed to stir for 18 hr and quenched with HCl (20 mL, 1 N) and extracted with ethyl acetate (2×30 ml). The organic layer was washed with saturated NH4Cl solution (25 mL), brine solution (25 mL) and dried over Na2SO4 and concentrated in vacuo to yield 4-Benzhydryloxy-1-benzyl-6-(4-fluoro-benzyl)-8-hydroxy-1H-1,3,6-triaza-s-indacene-5,7-dione 258 (94%, 103 mg, 0.188 mmol) as an off white oil. 1H NMR (300 MHz) CDCl3 δ 8.28 (bs, 1 H), 7.94 (s, 1 H), 7.89 (s, 1 H), 7.64-7.43 (m, 4 H), 7.17-7.43 (m, 12 H), 6.98-7.04 (s, 2 H), 5.57 (s, 2 H), 4.77 (s, 2 H). MS: 584.1 (M+1).

Workup

  1. customquenched with HCl (20 mL, 1 N)
  2. extractionextracted with ethyl acetate (2×30 ml)
  3. washThe organic layer was washed with saturated NH4Cl solution (25 mL), brine solution (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-363e52265c294b4d91055f56ad0545d7
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…