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Hydrochloric Acid → HCID 178483997、化合物

HRID 1257694
ノート
印刷プレビュー

反応式

HRID 1257694 の反応式
C1(S([N:10]2[CH:21]=[CH:20][C:19]3[C:11]2=[N:12][CH:13]=[C:14]2[C:18]=3[N:17]([C@H:22]3[CH2:26][CH2:25][C@H:24]([NH:27][C:28](=[O:36])[N:29]([CH3:35])[CH2:30][C:31]([F:34])([F:33])[F:32])[CH2:23]3)[N:16]=[N:15]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].Cl>CO.C1COCC1>[CH3:35][N:29]([CH2:30][C:31]([F:34])([F:32])[F:33])[C:28]([NH:27][C@H:24]1[CH2:25][CH2:26][C@H:22]([N:17]2[C:18]3[C:14](=[CH:13][N:12]=[C:11]4[C:19]=3[CH:20]=[CH:21][NH:10]4)[N:15]=[N:16]2)[CH2:23]1)=[O:36]
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 131730646racemic trans 3-[3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-1-methyl-1-(2,2,2-trifluoro-ethyl)-urea

生成物 1

HCID 178483997HCID 178483997、化合物収率 52.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

A solution of racemic trans 3-[3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-1-methyl-1-(2,2,2-trifluoro-ethyl)-urea (80.0 mg, 150 μmol) and sodium hydroxide solution (1.5 mL, 1N) in methanol (1 mL) and THF (1 mL) was stirred at ambient temperature for 30 minutes. Dilute HCl was added and the mixture purified by Isolute® SCX-2 column (gradient: methanol to 2M NH3 in methanol solution). The residue obtained was purified further by trituration with DCM/diethyl ether to afford 30 mg (51%) of racemic trans 1-methyl-3-[3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-1-(2,2,2-trifluoro-ethyl)-urea as a white solid. LCMS (Method A, ESI): RT=3.40 min, m+H=382.10; 1H NMR (400 MHz, DMSO) δ: 12.36 (s, 1H), 9.00 (s, 1H), 7.61 (t, 1H), 7.00 (dd, 1H), 6.67 (d, 1H), 5.66 (m, 1H), 4.41 (m, 1H), 4.09 (q, 2H), 2.97 (s, 3H), 2.50 (m, 2H), 2.27 (m, 3H), 1.79 (m, 1H).

後処理

  1. customthe mixture purified by Isolute® SCX-2 column (gradient: methanol to 2M NH3 in methanol solution)
  2. customThe residue obtained
  3. customwas purified further by trituration with DCM/diethyl ether

出典と根拠

ORDレコード
ord-1de3df66e89248d391cb86de601c2251
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461328B2

反応ノート

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