Potassium Phosphate, Tribasic → N-cyclopropyl-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

HRID 634215노트

반응식

HRID 634215 반응식
[CH:1]1([NH:4][C:5]2[O:6][C:7]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[N:15]([S:19]([C:22]3[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:14]=[C:13]4B3OC(C)(C)C(C)(C)O3)=[N:8][N:9]=2)[CH2:3][CH2:2]1.Cl[C:39]1[CH:44]=[N:43][CH:42]=[C:41]([CH:45]2[CH2:47][CH2:46]2)[N:40]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1([NH:4][C:5]2[O:6][C:7]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[N:15]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=3)(=[O:20])=[O:21])[CH:14]=[C:13]4[C:39]3[CH:44]=[N:43][CH:42]=[C:41]([CH:45]4[CH2:47][CH2:46]4)[N:40]=3)=[N:8][N:9]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 649849712-Chloro-6-cyclopropylpyrazineHCID 68328967N-cyclopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

생성물 1

HCID 68328339N-cyclopropyl-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine수율 19.5%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
130 °C

실험 절차

To a 20 mL microwave vial was added N-cyclopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (200 mg, 0.456 mmol), 2-chloro-6-cyclopropylpyrazine (CombiPhos Catalysts Inc., 78 mg, 0.502 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (13.05 mg, 0.027 mmol), Pd2(dba)3 (12.5 mg, 0.014 mmol), and potassium phosphate (291 mg, 1.369 mmol) followed by purging with argon. The solids were treated with dioxane (4.0 mL) and water (0.4 mL) and heated in the microwave at 130° C. for 20 min. The mixture was treated with H2O and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification (0-100% EtOAc in Hex) afforded N-cyclopropyl-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (45.6 mg, 19%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 513.1 (M+1).

후처리

  1. customby purging with argon
  2. additionThe solids were treated with dioxane (4.0 mL) and water (0.4 mL)
  3. additionThe mixture was treated with H2O
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification (0-100% EtOAc in Hex)

출처 및 근거

ORD 기록
ord-38f8414c7c6546f196110a7ad2b76f55
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321756B2

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