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Hydrochloric Acid → HCID 178483997, 화합물

HRID 1257694
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HRID 1257694 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 1

HCID 178483997HCID 178483997, 화합물수율 52.4%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1de3df66e89248d391cb86de601c2251
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461328B2

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