4-(Morpholinosulfonyl)aniline → 2-[4-(Morpholinosulfonyl)phenylamino]-6-(3-acetamidophenyl)pyrazine

HRID 16262

反応式

HRID 16262 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[O:18]1[CH2:23][CH2:22][N:21]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:20][CH2:19]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[O:18]1[CH2:19][CH2:20][N:21]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([NH:31][C:13]3[N:12]=[C:11]([C:7]4[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=4)[CH:16]=[N:15][CH:14]=3)=[CH:32][CH:33]=2)(=[O:26])=[O:25])[CH2:22][CH2:23]1

参加物

6

反応物 4

HCID 2107944-(Morpholinosulfonyl)anilineHCID 634876Binap, (A+-)-HCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23676156Sodium t-butoxide

生成物 1

HCID 115469622-[4-(Morpholinosulfonyl)phenylamino]-6-(3-acetamidophenyl)pyrazine収率 31.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Using Method L, 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 4-(morpholinosulfonyl) aniline (84.8 mg, 0.35 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 85° C. and kept for 16 hours. The same workup as for Method L followed by column chromatography afforded 34 mg of title compound. Yield: 31.2%. 1H NMR (250 MHz, DMSO-d6) δ 2.11 (s, 3 H), 2.86-2.89 (m, 4 H), 3.62-3.65 (m, 4 H), 7.45 (t, 1 H, 7.8 Hz), 7.54 (d, 1 H, 8.1 Hz), 7.73-7.80 (m, 3 H), 8.14 (d, 2 H, 8.9 Hz), 8.28 (s, 1 H), 8.57 (bs, 1 H), 8.61 (s, 1 H), 10.13 (s, 1 H), 10.18 (s, 1 H); 13C NMR (62.9 MHZ, DMSO-d6) δ 24.19, 45.90, 65.28, 117.09, 117.50, 120.06, 121.09, 125.43, 129.22, 129.33, 131.54, 134.02, 136.56, 140.07, 145.24, 147.83, 150.66, 168.57; m/z 454.2 [(M+H)+, calcd for C22H23N5O4S 453.2].

後処理

  1. customwere reacted at 85° C.

出典と根拠

ORDレコード
ord-b93f85af145e428bbb2aca044c4fb71b
出典データセット
uspto-grants-2010_06
特許番号
US07737152B2

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