Hydrochloric Acid → HCID 76284978, 화합물

HRID 1778769노트

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HRID 1778769 반응식
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[N:21](C3CCCCO3)[N:20]=[C:19](I)[C:16]2=[N:17][CH:18]=1.[CH3:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.C(Cl)(=O)C>O1CCOCC1.O.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[NH:21][N:20]=[C:19]([C:33]3[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=3)[C:16]2=[N:17][CH:18]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86722865HCID 86722865, 화합물

생성물 1

HCID 76284978HCID 76284978, 화합물수율 20.5%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매2회HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-b]pyridine (25 mg, 0.047 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (12 mg, 0.056 mmol), tetrakis(triphenylphosphine)palladium(0) (3 mg, 0.002 mmol), and cesium carbonate (46 mg, 0.14 mmol) in 1,4-dioxane (0.5 mL) and water (0.07 mL) in a reaction vial was degassed, sealed, and stirred at 85° C. for 3 h. After cooling the mixture was concentrated and the residue was dissolved in methanol (0.4 mL, 10 mmol). To the solution was added HCl solution previously prepared from acetyl chloride (0.3 mL) in methanol (0.3 mL). The mixture was stirred at r.t. for 1 h then concentrated, diluted with methanol, and purified by RP-HPLC (pH=2) to afford the desired product (3.9 mg) as a TFA salt. LCMS (M+H)+=404.1.

후처리

  1. customin a reaction
  2. customvial was degassed
  3. customsealed
  4. temperatureAfter cooling the mixture
  5. concentrationwas concentrated
  6. stirringThe mixture was stirred at r.t. for 1 h
  7. concentrationthen concentrated
  8. additiondiluted with methanol
  9. custompurified by RP-HPLC (pH=2)

출처 및 근거

ORD 기록
ord-352e8a6c4178457794ddb81fc7d4ddf8
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266892B2

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