Hydrochloric Acid → 6-Chloro-16-oxa-2,4,8,26-tetraazatetracyclo[18.3.1.1(3,7).1(11,15)]hexacosa-1(24),3(26),4,6,11(25),12,14,20,22-nonaene

HRID 1614963노트

반응식

HRID 1614963 반응식
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[C:15]([Cl:28])=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1.[OH-].[Na+].Cl>O1CCCC1.O>[Cl:28][C:15]1[CH:14]=[N:13][C:12]2[NH:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([CH:6]=3)[CH2:4][CH2:3][CH2:2][O:27][C:23]3[CH:22]=[C:21]([CH2:20][CH2:19][NH:18][C:16]=1[N:17]=2)[CH:26]=[CH:25][CH:24]=3

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 584678483-{2-[(2-{[3-(3-Bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

생성물 1

HCID 468647456-Chloro-16-oxa-2,4,8,26-tetraazatetracyclo[18.3.1.1(3,7).1(11,15)]hexacosa-1(24),3(26),4,6,11(25),12,14,20,22-nonaene수율 10%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-{2-[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol (50.0 mg, 0.108 mmol) in tetrahydrofuran (1.0 mL) was added a solution of sodium hydroxide in water (1.0 mL, 1.0 M). The resultant solution was stirred at rt for 60 hours until the reaction was complete. The reaction mixture 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 a residue, which was purified by silica gel column chromatography to give the desired product as a white powder (4.0 mg, 10%). LCMS for C21H22ClN4O (M+H)+: m/z=381.0. 1H NMR (400 MHz, CD3OD): δ 7.95 (s, 1H), 7.90 (s, 1H), 7.30 (m, 3H), 7.12 (t, J=7.4 Hz, 1H), 6.94 (m, 1H), 6.65 (m, 2H), 3.70 (t, J=7.6 Hz, 2H), 3.48 (t, J=6.8 Hz, 2H), 2.80 (m, 2H), 2.72 (m, 2H), 2.10 (m, 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 a residue, which
  6. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-718ec02163de452a94eebc2970e36c8e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765727B2

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