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Diisopropylethylamine → 4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]thiophene-2-carboxamide

HRID 1255860
ノート
印刷プレビュー

反応式

HRID 1255860 の反応式
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:18]=[C:19]([C:22]([OH:24])=O)[S:20][CH:21]=3)[CH:13]=2)[CH:3]=1.[F:25][C:26]([F:37])([F:36])[CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=1)[NH2:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:18]=[C:19]([C:22]([NH:28][CH:27]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=4)[C:26]([F:25])([F:36])[F:37])=[O:24])[S:20][CH:21]=3)[CH:13]=2)[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 649850182,2,2-Trifluoro-1-(6-methyl-pyridin-2-YL)-ethylamineHCID 687770504-(6-Pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)thiophene-2-carboxylic acid hydrochloride

生成物 1

HCID 68775719
4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]thiophene-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)thiophene-2-carboxylic acid hydrochloride (20 mg, 0.06 mmol), 2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethanamine (step C, 12 mg, 0.06 mmol), BOP (41 mg, 0.09 mmol) and N,N-diisopropylethylamine (16 □L, 0.09 mmol) in DMF (0.6 mL) was stirred at 40° C. for 4 hours. The reaction was partitioned between water and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated in vacuo. Purification by reverse phase LC gave 4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]thiophene-2-carboxamide. 1H NMR (600 MHz, CDCl3): δ 9.42 (bs, 1H), 9.11 (s, 1H), 9.00 (d, J=2.4 Hz, 1H), 8.84 (d, J=5.3 Hz, 1H), 8.81 (d, J=2.3 Hz, 1H), 8.55 (s, 2H), 8.34 (d, J=8.3 Hz, 1H), 8.17 (s, 1H), 7.99 (t, J=8.5 Hz, 1H), 7.85 (dd, J=7.9, 5.3 Hz, 1H), 7.58 (d, J=7.4 Hz, 1H), 7.48 (m, 1H), 6.13 (m, 1H), 3.48 (s, 3H). LC-MS EIMS: m/z 495.1 [M+H]+.

後処理

  1. customThe reaction was partitioned between water and ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by reverse phase LC

出典と根拠

ORDレコード
ord-f408713b961f48d7979aa1eb516fe821
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461162B2

反応ノート

読み込み中…

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