Cesium carbonate → (6-(5-Carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonic acid

HRID 1798322노트

반응식

HRID 1798322 반응식
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][S:14]([O:17]C)(=[O:16])=[O:15])[O:3]1.Cl[C:20]1[S:24][C:23]([C:25]([NH2:27])=[O:26])=[N:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:25]([C:23]1[S:24][C:20]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[CH:4]([CH2:13][S:14]([OH:17])(=[O:15])=[O:16])[O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[N:21][N:22]=1)(=[O:26])[NH2:27]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 123487555-Chloro-1,3,4-thiadiazole-2-carboxamideHCID 58292585Methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

생성물 1

HCID 58292845(6-(5-Carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate (0.46 g, 1.71 mmol, 1 eq.) and 5-chloro-1,3,4-thiadiazole-2-carboxamide (0.42 g, 2.56 mmol, 1.5 eq.) in 10 ml DMF was added cesium carbonate (2.22 g, 6.82 mmol, 4 eq.) portionwise. The reaction was stirred at room temperature overnight. It was then quenched by water, extracted with EtOAc. The aqueous layer was collected and prep HPLC gave the product as white flakes. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.01 (s, 1H), 7.39 (d, J=2.4 Hz, 1H), 7.27 (d, J=2.4 Hz, 1H), 5.42 (d, 7.6 Hz, 1H), 3.04 (dd, J=14.4, 1.2 Hz, 1H), 2.46 (m, 1H), 2.27 (s, 3H).

후처리

  1. customIt was then quenched by water
  2. extractionextracted with EtOAc
  3. customThe aqueous layer was collected
  4. customprep HPLC gave the product as white flakes

출처 및 근거

ORD 기록
ord-74a5c80557dc4d56891db6bf9cc65dc5
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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