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 1614951ノート

反応式

HRID 1614951 の反応式
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

参加物

6

反応物 3

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

生成物 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-nonaene収率 21%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6ce15d9273a94aa9b53998e72517b1ff
出典データセット
uspto-grants-2014_07
特許番号
US08765727B2

反応ノート

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