Cesium carbonate → HCID 67353704, compound

HRID 75849Notes

Reaction equation

HRID 75849 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:31]1[S:32][C:33]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:34]=2[N:35]=1>>[F:40][C:38]1[CH:37]=[CH:36][C:34]2[N:35]=[C:31]([O:1][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=4)=[CH:4][CH:3]=3)[S:32][C:33]=2[CH:39]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 20498702-Chloro-6-fluorobenzothiazoleHCID 136337389Methyl 2-(3-(4-hydroxyphenyl)isoxazole-5-carboxamido)-3-methylbutanoate

Product 1

HCID 67353704HCID 67353704, compound

Procedure

To methyl 2-(3-(4-hydroxyphenyl)isoxazole-5-carboxamido)-3-methylbutanoate (200 mg) in N,N′-Dimethyl formamide (4 ml), cesium carbonate (245 mg) was added and stirred for 15-20 minutes. To this 2-chloro-6-fluorobenzo[d]thiazole (141 mg) was added and the reaction mixture was stirred at RT for 18 hours. Solvent was evaporated to obtain pale brown solid, which was purified by column chromatography (silica gel, EtOAc—CHCl3) to obtain off white solid, which was crystallized using DCM-Petroleum ether to obtain the title compound as white solid. Yield: 240 mg (81%); MS (ES+): m/z 470 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 9.27 (d, 1H), 8.08 (d, 2H), 7.93 (dd, 1H), 7.8 (s, 1H), 7.74 (dd, 1H), 7.67 (d, 2H), 7.31 (m, 1H), 4.33 (m, 1H), 3.69 (s, 3H), 2.23 (m, 1H), 0.98 (d, 6H).

Workup

  1. stirringthe reaction mixture was stirred at RT for 18 hours
  2. customSolvent was evaporated
  3. customto obtain pale brown solid, which
  4. customwas purified by column chromatography (silica gel, EtOAc—CHCl3)
  5. customto obtain off white solid, which
  6. customwas crystallized

Sources & evidence

ORD record
ord-6d636cdc41314dff88794295f601e762
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

Loading…