Hydrochloric Acid → 6-Chloro-16-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(11,15)]pentacosa-1(23),3(25),4,6,11(24),12,14,19,21-nonaene

HRID 1614951노트

반응식

HRID 1614951 반응식
Br[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[C:14]([Cl:27])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].Cl>O1CCCC1.O>[Cl:27][C:14]1[CH:13]=[N:12][C:11]2[NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH:5]=3)[CH2:3][CH2:2][O:26][C:22]3[CH:21]=[C:20]([CH2:19][CH2:18][NH:17][C:15]=1[N:16]=2)[CH:25]=[CH:24][CH:23]=3

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 584678313-{2-[(2-{[3-(2-Bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

생성물 1

HCID 468647056-Chloro-16-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(11,15)]pentacosa-1(23),3(25),4,6,11(24),12,14,19,21-nonaene수율 21%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-{2-[(2-{[3-(2-bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol (50.0 mg, 0.112 mmol) in tetrahydrofuran (1.09 mL) was added a solution of sodium hydroxide in water (0.893 mL, 0.50 M). The resultant solution was stirred at rt for 2 days until the reaction was complete. The reaction was neutralized with HCl (3 M, aqueous solution) to pH 7. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (8.5 mg, 21%). LCMS for C20H20ClN4O (M+H)+: m/z=367.0. 1H NMR (400 MHz, CD3OD): δ 7.81 (s, 1H), 7.70 (s, 1H), 7.57 (m, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.08 (m, 2H), 6.69 (s, 1H), 6.67 (m, 2H), 5.73 (dd, J=6.8, 0.8 Hz, 2H), 5.14 (dd, J=7.2, 1.2 Hz, 2H), 3.72 (t, J=7.6 Hz, 2H), 2.86 (t, J=7.6 Hz, 2H).

후처리

  1. extractionThe aqueous layer was extracted with EtOAc twice
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude, which
  6. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6ce15d9273a94aa9b53998e72517b1ff
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765727B2

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