Azetidine → 1-[2-(2-Chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidin-7-yl]-3-ethylaminoazetidine-3-carboxylic Acid Amide

HRID 348027노트

반응식

HRID 348027 반응식
Cl.[CH2:2]([NH:4][C:5]1([C:9]([NH2:11])=[O:10])[CH2:8][NH:7][CH2:6]1)[CH3:3].C(N(C(C)C)CC)(C)C.Cl[C:22]1[N:27]2[N:28]=[C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[C:30]([I:31])=[C:26]2[N:25]=[CH:24][CH:23]=1.N1CCC1>CC(C)=O>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:29]1[C:30]([I:31])=[C:26]2[N:25]=[CH:24][CH:23]=[C:22]([N:7]3[CH2:8][C:5]([NH:4][CH2:2][CH3:3])([C:9]([NH2:11])=[O:10])[CH2:6]3)[N:27]2[N:28]=1

참가 물질

6

반응물 4

HCID 10422AzetidineHCID 81531Diisopropylethylamine2회HCID 21083717HCID 21083717, 화합물HCID 692108943-(ethylamino)-3-Azetidinecarboxamide hydrochloride

생성물 1

HCID 588013161-[2-(2-Chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidin-7-yl]-3-ethylaminoazetidine-3-carboxylic Acid Amide

시약·촉매·용매 1

HCID 180Acetone용매

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온도
50 °C

실험 절차

To a slurry of 3-ethylaminoazetidine-3-carboxylic acid amide, hydrochloride salt (I-1A-3e; 1.13 g, 5.2 mmol) and diisopropylethylamine (3.2 ml, 18 mmol) in acetone (60 ml) was added 7-chloro-2-(2-chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidine (I-1A-1d; 1.36 g, 3.48 mmol). The mixture was heated to 50° C. overnight. Additional azetidine and diisopropylethylamine were added in portions until the reaction was judged complete by LCMS. A pale yellow precipitate formed and was isolated by vacuum filtration. The filtrate was concentrated to 20 ml and then diluted with diethyl ether to precipitate additional material that was collected by vacuum filtration. The combined solids were triturated from ether to afford product I-2A-1a as a pale yellow solid (1.3 g, 76%): +ESI MS (M+1) 497.0; 1H NMR (400 MHz, DMSO-D6) δ 8.27 (d, J=5.4 Hz, 1H), 7.59 (d, J=7.9 Hz, 1H), 7.52–7.44 (m, 3H), 7.35 (br s, 1H), 7.30 (br s, 1H), 5.98 (d, J=5.0 Hz, 1H), 2.40–2.30 (m, 2H), 0.99 (t, J=7.1 Hz, 3H).

후처리

  1. customA pale yellow precipitate formed
  2. customwas isolated by vacuum filtration
  3. concentrationThe filtrate was concentrated to 20 ml
  4. additiondiluted with diethyl ether
  5. customto precipitate additional material that
  6. filtrationwas collected by vacuum filtration
  7. customThe combined solids were triturated from ether
  8. customto afford product

출처 및 근거

ORD 기록
ord-230ce8f19e034f43b442b399847c7f8c
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176210B2

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