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

HRID 348027ノート

反応式

HRID 348027 の反応式
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

参加物

6

反応物 4

HCID 10422AzetidineHCID 81531Diisopropylethylamine2 回HCID 21083717HCID 21083717、化合物HCID 692108943-(ethylamino)-3-Azetidinecarboxamide hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-230ce8f19e034f43b442b399847c7f8c
出典データセット
uspto-grants-2007_02
特許番号
US07176210B2

反応ノート

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