Triethylamine → 1-(benzo[d][1,3]dioxol-5-yl)-N-(4-(2-methylthiazol-4-yl)phenyl)cyclopropane-carboxamide

HRID 39174

反応式

HRID 39174 の反応式
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[N:6]=1.[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3([C:26](O)=[O:27])[CH2:25][CH2:24]3)=[CH:22][C:17]=2[O:16][CH2:15]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C>[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3([C:26]([NH:11][C:10]4[CH:12]=[CH:13][C:7]([C:5]5[N:6]=[C:2]([CH3:1])[S:3][CH:4]=5)=[CH:8][CH:9]=4)=[O:27])[CH2:24][CH2:25]3)=[CH:22][C:17]=2[O:16][CH2:15]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 1526842-Methyl-4-(4-aminophenyl)thiazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acid

生成物 1

HCID 592061661-(benzo[d][1,3]dioxol-5-yl)-N-(4-(2-methylthiazol-4-yl)phenyl)cyclopropane-carboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-(2-Methylthiazol-4-yl)aniline (19 mg, 0.10 mmol) and 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (20.6 mg, 0.100 mmol) were dissolved in acetonitrile (1.0 mL) containing triethylamine (42 μL, 0.30 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (42 mg, 0.11 mmol) was added to the mixture and the resulting solution was allowed to stir for 16 hours. The crude product was purified by reverse-phase preparative liquid chromatography to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(4-(2-methylthiazol-4-yl)phenyl)cyclopropane-carboxamide. ESI-MS m/z calc. 378.1, found; 379.1 (M+1)+; Retention time 2.72 minutes. 1H NMR (400 MHz, DMSO-d6) δ 1.04-1.10 (m, 2H), 1.40-1.44 (m, 2H), 2.70 (s, 3H), 6.03 (s, 2H), 6.88-6.96 (m, 2H), 7.01 (d, J=1.4 Hz, 1H), 7.57-7.61 (m, 2H), 7.81-7.84 (m, 3H), 8.87 (s, 1H).

後処理

  1. customThe crude product was purified by reverse-phase preparative liquid chromatography

出典と根拠

ORDレコード
ord-2e2fbb834fa5474a8078a7cad1abd022
出典データセット
uspto-grants-2013_09
特許番号
US08524767B2

関連ノート

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