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Triethylamine → N-(4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)ethenesulfonamide

HRID 530967
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HRID 530967 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32].C(=O)(O)[O-].[Na+]>ClCCl>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:31]([CH:30]=[CH2:29])(=[O:33])=[O:32])=[CH:3][CH:4]=3)[C:16]=12
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 516892Sodium BicarbonateHCID 585067963-(4-aminophenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

생성물 1

HCID 54756018N-(4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)ethenesulfonamide수율 16%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

A solution of dichloromethane (5 mL), compound 23 (45 mg, 0.168 mmol) and triethylamine (71 μL, 0.509 mmol) was cooled to 0° C. 2-chloro-1-ethane sulfonyl chloride (16 μL, 0.148 mmol) was added and the reaction was allowed to proceed for 1 hour prior to addition of saturated sodium bicarbonate (10 mL) and extraction with dichloromethane (2×10 mL). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo. The product was purified by preparative RP-HPLC and lyophilized (8.7 mg, 16% yield): 1H NMR (400 MHz, DMSO) δ 10.30 (s, 1H), 8.36 (s, 1H), 7.60 (d, J=8.5, 2H), 7.31 (d, J=8.6, 2H), 6.86 (dd, J=16.4, 9.9, 1H), 6.21 (d, J=16.4, 1H), 6.09 (d, J=9.9, 1H), 5.08 (hept, J=6.7, 2H), 1.49 (d, J=6.7, 6H); 13C NMR (100 MHz, DMSO) δ 155.44, 152.03, 151.64, 144.22, 138.54, 136.17, 129.25, 127.98, 127.41, 119.52, 96.95, 48.66, 21.75; [M+H]+ calculated for C16H18N6O2S 359.1, found 359.5.

후처리

  1. dry with materialThe combined organic layers were dried with MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by preparative RP-HPLC

출처 및 근거

ORD 기록
ord-cbbe8363af9c4ba2b7f0f42cfd19f1f5
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353116B2

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