Potassium Carbonate → 3-Chloro-N-[6-methyl-3-[3-(4-morpholinyl)phenyl]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

HRID 573676노트

반응식

HRID 573676 반응식
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:22])=[CH:8][C:9]=2[NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)(=[O:14])=[O:13])[S:4][C:3]=1[C:23]1[CH:24]=[N:25][N:26](C(OC(C)(C)C)=O)[CH:27]=1.[O:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=2)[CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.CN(C=O)C>[Cl:21][C:17]1[CH:16]=[C:15]([S:12]([NH:11][C:9]2[CH:8]=[C:7]([CH3:22])[N:6]=[C:5]3[S:4][C:3]([C:23]4[CH:27]=[N:26][NH:25][CH:24]=4)=[C:2]([C:45]4[CH:44]=[CH:43][CH:42]=[C:41]([N:38]5[CH2:37][CH2:36][O:35][CH2:40][CH2:39]5)[CH:46]=4)[C:10]=23)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 41926613-(Morpholino)phenylboronic acidHCID 683240291,1-Dimethylethyl 4-(3-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridin-2-yl)-1H-pyrazole-1-carboxylate

생성물 1

HCID 683237523-Chloro-N-[6-methyl-3-[3-(4-morpholinyl)phenyl]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A mixture of 1,1-dimethylethyl 4-(3-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridin-2-yl)-1H-pyrazole-1-carboxylate (Description 75) (100 mg, 0.171 mmol), 3-(morpholino)phenylboronic acid, pinacol ester (99 mg, 0.343 mmol), tetrakis(triphenylphosphine)palladium(0) (19.79 mg, 0.017 mmol), bis(triphenylphosphine)palladium(II) chloride (12.02 mg, 0.017 mmol) and potassium carbonate (71.0 mg, 0.514 mmol) were weighed into a microwave vial. 1,4-Dioxane (1.5 mL), DMF (0.75 mL) and water (0.38 mL) were added and the mixture heated in a microwave at 120° C. for 15 min. At this point, the five reaction mixtures were combined and concentrated. The residue was passed through an SCX cartridge, eluting with MeOH (150 mL) and then 2M NH3 in MeOH (200 mL). The basic methanolic solution was concentrated and the residue was purified by MDAP (acidic conditions), to give the title compound (115 mg).

후처리

  1. customAt this point, the five reaction mixtures
  2. concentrationconcentrated
  3. washeluting with MeOH (150 mL)
  4. concentrationThe basic methanolic solution was concentrated
  5. customthe residue was purified by MDAP (acidic conditions)

출처 및 근거

ORD 기록
ord-5eef735ff84540a6a467e354b3d6ba5c
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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