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Dabco → 1-(4-(9-(Dicyclopropylmethyl)-8-ethyl-9H-purin-6-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea

HRID 2117076
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HRID 2117076 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:22]([NH:24][C:25](=[O:34])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[S:23])[CH:5]=[CH:6][C:7]=1[O:8]C1C2=C(C)C(OC)=CN2N=CN=1.Cl[C:36]1[N:44]=[CH:43][N:42]=[C:41]2[C:37]=1[N:38]=[C:39]([CH2:52][CH3:53])[N:40]2[CH:45]([CH:49]1[CH2:51][CH2:50]1)[CH:46]1[CH2:48][CH2:47]1.N12CCN(CC1)CC2>CC#N>[CH:46]1([CH:45]([CH:49]2[CH2:51][CH2:50]2)[N:40]2[C:39]([CH2:52][CH3:53])=[N:38][C:37]3[C:41]2=[N:42][CH:43]=[N:44][C:36]=3[O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:21][C:22]([NH:24][C:25](=[O:34])[CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[S:23])=[CH:3][C:2]=2[F:1])[CH2:48][CH2:47]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 9237DabcoHCID 116271861-(3-Fluoro-4-(6-methoxy-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea2회HCID 221436956-Chloro-9-dicyclopropylmethyl-8-ethylpurine

생성물 1

HCID 117138301-(4-(9-(Dicyclopropylmethyl)-8-ethyl-9H-purin-6-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea수율 36%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

To a mixture 1-(3-fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea (24 mg, 0.075 mmol, Compound A of Example 3), 6-chloro-9-(dicyclopropylmethyl)-8-ethyl-9H-purine (20.7 mg, 0.075 mmol, PCT Appl. WO 99/01454, U.S. Pat. No. 6,143,743, example 831, the disclosure of which is herein incorporated by reference) and 1,4-diazabicyclo[2.2.2]octane (DABCO, 8.4 mg, 0.075 mmol) was added MeCN (2 mL). The reaction was stirred at RT for 4 h and concentrated in vacuo. The residue was purified by reverse phased preparative HPLC to give the title compound (15.3 mg, 36%) as a white solid. 1H NMR (CDCl3) δ 12.43 (m, 1H), 8.48 (m, 1H), 8.40 (m, 1H), 7.92 (m, 1H), 7.28 (m, 4H), 7.13 (m, 2H), 3.72 (s, 2H), 3.34 (m, 3H), 1.53 (m, 3H), 0.81 (m, 2H), 0.46 (m, 4H), 0.23 (m, 2H), MS(ESI+) m/z 489 (M+H)+.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by reverse

출처 및 근거

ORD 기록
ord-fb8869a026414c85830309a621dbe954
출처 데이터셋
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07439246B2

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