Diisopropylethylamine → S-Isopropyl 4-(3-bromoimidazo[1,2-b]pyridazin-6-yl)piperazine-1-carbothioate

HRID 870757ノート

反応式

HRID 870757 の反応式
CCN(C(C)C)C(C)C.[C:10](=[O:16])(Cl)[S:11][CH:12]([CH3:14])[CH3:13].[Br:17][C:18]1[N:22]2[N:23]=[C:24]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:25]=[CH:26][C:21]2=[N:20][CH:19]=1>C(OCC)(=O)C>[Br:17][C:18]1[N:22]2[N:23]=[C:24]([N:27]3[CH2:28][CH2:29][N:30]([C:10](=[O:16])[S:11][CH:12]([CH3:14])[CH3:13])[CH2:31][CH2:32]3)[CH:25]=[CH:26][C:21]2=[N:20][CH:19]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 13279441S-Isopropyl chlorothioformateHCID 866964323-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine

生成物 1

HCID 86696466S-Isopropyl 4-(3-bromoimidazo[1,2-b]pyridazin-6-yl)piperazine-1-carbothioate収率 78.5%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Hunig's base [7087-68-5] (0.4 mL, 2.4 mmol), then S-isopropyl carbonochloridothioate [13889-93-5] (0.2 mL, 1.6 mmol) were added to a stirred, ambient temperature solution of 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine (450.0 mg, 1.6 mmol) in ethyl acetate (30 mL). Then rapidly formed suspension was stirred overnight, under N2 blanket, then washed with brine, dried (MgSO4), evaporated, and crystallized from ethyl acetate/heptane to afford 482.9 mg of white powder, mp. 186-187° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (d, J=6.82 Hz, 6H) 2.51 (dt, J=3.60, 1.86 Hz, 1H) 3.49-3.59 (m, 1H) 3.59-3.71 (m, 7H) 7.58 (d, J=9.85 Hz, 1H) 8.09-8.13 (m, 2H). 13C NMR (100 MHz, DMSO-d6) δ ppm 23.22, 35.48, 44.71, 101.63, 110.84, 113.71, 114.69, 116.58, 119.46, 123.56, 126.04, 134.22, 155.61, 157.77, 158.15, 158.53, 158.90, 166.18. LRMS (ESI) m/z 384.0/386.0 [(M+H)]+, calc'd for C14H15BrN6OS: 384.30.

後処理

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customcrystallized from ethyl acetate/heptane

出典と根拠

ORDレコード
ord-f3fabef5445a4afe9f7f8e00209290c1
出典データセット
uspto-grants-2015_03
特許番号
US08969565B2

反応ノート

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