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Hydrochloric Acid → 19-Chloro-9-oxa-2,17,21,22-tetraazatetracyclo[16.3.1.1(3,7).1(10,14)]tetracosa-1(22),3(24),4,6,10(23),11,13,18,20-nonaene

HRID 1614948
ノート
印刷プレビュー

反応式

HRID 1614948 の反応式
Br[CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][C:19]3[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=3)[C:13]([Cl:26])=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Cl>O1CCCC1.O>[Cl:26][C:13]1[CH:12]=[N:11][C:10]2=[N:15][C:14]=1[NH:16][CH2:17][CH2:18][C:19]1[CH:20]=[C:21]([O:25][CH2:2][C:3]3[CH:4]=[C:5]([NH:9]2)[CH:6]=[CH:7][CH:8]=3)[CH:22]=[CH:23][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 584678503-{2-[(2-{[3-(Bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

生成物 1

HCID 4686470419-Chloro-9-oxa-2,17,21,22-tetraazatetracyclo[16.3.1.1(3,7).1(10,14)]tetracosa-1(22),3(24),4,6,10(23),11,13,18,20-nonaene収率 65%

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-(bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol (25.0 mg, 0.0576 mmol) in tetrahydrofuran (0.561 mL) was added a solution of sodium hydroxide in water (0.46 mL, 0.50 M). The resultant solution was stirred at rt for 16 hours until the reaction was complete. The reaction mixture was neutralized with aqueous HCl solution (3 M) to pH 7. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as an off-white powder (13 mg, 65%). LCMS for C19H18ClN4O (M+H)+: m/z=353.0. 1H NMR (400 MHz, CD3OD): δ 7.72 (s, 1H), 7.52 (s, 1H), 7.29 (t, J=7.6 Hz, 1H), 7.19 (s, 1H), 7.10 (dd, J=7.6, 0.8 Hz, 1H), 7.06 (t, J=7.2 Hz, 1H), 6.93 (dd, J=7.2, 0.8 Hz, 1H), 6.73 (dd, J=2.4, 0.8 Hz, 1H), 6.66 (d, J=7.2 Hz, 1H), 5.25 (s, 2H), 3.70 (m, 2H), 2.72 (t, J=6.8 Hz, 1H).

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. customthen triturated with cold EtOAc)

出典と根拠

ORDレコード
ord-ada7f289380348e0bb86b47e9f3075a9
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765727B2

反応ノート

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