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Dichloromethane → N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide

HRID 1484960
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HRID 1484960 반응식
C(Cl)Cl.Br[C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:16]=[C:15]([C@@H:17]3[CH2:19][C@H:18]3[CH3:20])[NH:14][N:13]=2)[C:8]([Cl:21])=[CH:7][N:6]=1.[C:22]([NH:26][S:27]([C:30]1[S:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:22]([NH:26][S:27]([C:30]1[S:34][C:33]([C:5]2[N:10]=[C:9]([NH:11][C:12]3[CH:16]=[C:15]([C@@H:17]4[CH2:19][C@H:18]4[CH3:20])[NH:14][N:13]=3)[C:8]([Cl:21])=[CH:7][N:6]=2)=[CH:32][CH:31]=1)(=[O:28])=[O:29])([CH3:25])([CH3:23])[CH3:24]
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참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 581692085-(N-tert-butylsulfamoyl)thiophen-2-ylboronic acidHCID 866515532-bromo-5-chloro-N-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-yl)pyrimidin-4-amine

생성물 1

HCID 66927457N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide수율 63.2%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

The mixture of Pd(dppf)Cl2.CH2Cl2 (74 mg, 0.09 mmol, 0.15 eq.), 2-bromo-5-chloro-N-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-yl)pyrimidin-4-amine (200 mg, 0.61 mmol, 1.0 eq), 5-(N-tert-butylsulfamoyl)thiophen-2-ylboronic acid (192 mg, 0.73 mmol, 1.2 equiv.) and saturate Ka2CO3 (5 mL) in dioxane (10 mL) was heated to 90° C. for 1 h under nitrogen atmosphere. The reaction mixture was cooled to rt, and extracted with THF. The combined layers were purified by silica gel chromatography (EtOAc/Petroleum ether from 10:1 to 2:1) to afford compound N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (180 mg, 63%).

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with THF
  3. customThe combined layers were purified by silica gel chromatography (EtOAc/Petroleum ether from 10:1 to 2:1)

출처 및 근거

ORD 기록
ord-370bc7a81aeb4f449cbceef7543f95ca
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09422271B2

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