Potassium Phosphate, Tribasic → Ethyl 7-(2-(3-ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)-2-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-2-carboxylate

HRID 712316노트

반응식

HRID 712316 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:10]2[S:14][C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:12][C:11]=2[CH:21]=1)(=O)=O.[CH3:30][C:31]1([C:51]([O:53][CH2:54][CH3:55])=[O:52])[O:36][C:35]2[CH:37]=[C:38](B3OC(C)(C)C(C)(C)O3)[CH:39]=[N:40][C:34]=2[NH:33][C:32]1=[O:50].ClC1N2N=C(N)N=C2C=C(Cl)C=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O>[CH2:19]([NH:18][C:16](=[O:17])[NH:15][C:13]1[S:14][C:10]2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:8][C:7]([C:38]3[CH:39]=[N:40][C:34]4[NH:33][C:32](=[O:50])[C:31]([CH3:30])([C:51]([O:53][CH2:54][CH3:55])=[O:52])[O:36][C:35]=4[CH:37]=3)=[CH:21][C:11]=2[N:12]=1)[CH3:20]

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 594375625,7-Dichloro-[1,2,4]triazolo[1,5-A]pyridin-2-amineHCID 66977204ethyl 2-methyl-3-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-2-carboxylateHCID 72724619HCID 72724619, 화합물

생성물 1

HCID 86664029Ethyl 7-(2-(3-ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)-2-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-2-carboxylate수율 42%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To the solution of 2-(3-ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl trifluoromethanesulfonate (0.5 g, 1.12 mmol) and ethyl 2-methyl-3-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-2-carboxylate (0.4 g, 1.12 mmol) in 1,4-dioxane:MeOH (5:3 mL) was added potassium phosphate (0.36 g, 1.68 mmol) at rt and the mixture degassed for 15-20 min by purging N2 followed by the addition of dichloro(1,1-bis(diphenylphosphino)(ferrocene)palladium (II) (0.091 g, 0.11 mmol). The reaction was degassed for another 15-20 min then heated to 80° C. for 5 h. After completion of reaction (by TLC), the reaction was cooled to rt, diluted with EtOAc (500 mL), passed through celite, the filtrate concentrated under reduced pressure and the crude residue purified over 100-200 M silica-gel using eluent 2.3% MeOH: DCM to obtain the desired product as an off-white solid (0.25 g, 42%). 1H NMR (DMSO-d6): δ 1.06-1.13 (m, 6H), 1.77 (s, 3H), 3.21 (q, J=7.20, 2H), 4.14 (m, 2H), 6.87 (br s, 1H), 7.45 (m, 1H), 7.97-8.03 (m, 2H), 8.09 (s, 1H), 8.29 (s, 1H), 8.55 (s, 2H), 8.80 (d, J=4.0 Hz, 1H), 10.62 (br s, 1H) and 11.73 (br s, 1H). MS: 533.24 [M+H]+.

후처리

  1. customthe mixture degassed for 15-20 min
  2. customby purging N2
  3. customThe reaction was degassed for another 15-20 min
  4. customAfter completion of reaction (by TLC)
  5. temperaturethe reaction was cooled to rt
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customthe crude residue purified over 100-200 M silica-gel

출처 및 근거

ORD 기록
ord-cad16fdd0f1e4f62875d48f437be9442
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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