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

HRID 870757노트

반응식

HRID 870757 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f3fabef5445a4afe9f7f8e00209290c1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

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