Dimethylformamide → HCID 46852668、化合物

HRID 1262093ノート

反応式

HRID 1262093 の反応式
[CH3:1][S:2]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20](O)=[N:21]3)=[CH:16][CH:15]=2)[CH2:6]1)(=[O:4])=[O:3].C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C.CN(C)C=O.[NH2:59][C:60]1[CH:65]=[CH:64][C:63]([CH:66]2[CH2:69][N:68]([CH2:70][C:71]([NH2:73])=[O:72])[CH2:67]2)=[CH:62][CH:61]=1>>[CH3:1][S:2]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20]([NH:59][C:60]4[CH:65]=[CH:64][C:63]([CH:66]5[CH2:67][N:68]([CH2:70][C:71]([NH2:73])=[O:72])[CH2:69]5)=[CH:62][CH:61]=4)=[N:21]3)=[CH:16][CH:15]=2)[CH2:6]1)(=[O:3])=[O:4]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 574160632-[3-(4-Aminophenyl)azetidin-1-yl]acetamideHCID 178504916HCID 178504916、化合物

生成物 1

HCID 46852668HCID 46852668、化合物収率 7.7%

実験手順

7-(2-Methanesulfonyl-2,3-dihydro-1H-isoindol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (80 mg, 0.2 mmol), N-Phenylbis(trifluoromethanesulphonimide) (95.1 mg, 0.266 mmol), N,N-Diisopropylethylamine (0.126 mL, 0.726 mmol), and N,N-Dimethylformamide (2 mL, 30 mmol) and stir at room temperature for half an hour. Add 2-[3-(4-Amino-phenyl)-azetidin-1-yl]-acetamide (71 mg, 0.34 mmol) and stir at 60° C. overnight. The reaction was concentrated, DMSO added, filtered and placed onto the Gilson for purification. The most pure fractions were collected, basified with sat sodium bicarbonate extracted with EtOAc, dried, filtered and concentrated to give a yellow solid (8 mg, 6%). MP 216-218° C. LCMS (E/I+) 518 (M+H). NMR 1H (DMSO-d6)-9.48 (s, 1H), 9.02 (s, 1H), 7.97 (d, 1H, J=7.81 Hz), 7.64 (d, 2H, J=8.55 Hz), 7.56 (t, 1H, J=7.80 Hz), 7.44 (d, 1H, J=7.74 Hz), 7.21 (d, 2H, J=8.34 Hz), 7.12 (bs, 1H), 7.05-7.08 (m, 2H), 6.99 (d, 1H, J=4.69 Hz), 4.74 (s, 4H), 3.69 (t, 2H, J=7.40 Hz), 3.53-3.61 (m, 1H), 3.15 (t, 2H, J=6.86 Hz), 3.02 (s, 2H), 2.92 (s, 3H).

後処理

  1. concentrationThe reaction was concentrated
  2. additionDMSO added
  3. filtrationfiltered
  4. customplaced onto the Gilson for purification
  5. customThe most pure fractions were collected
  6. extractionextracted with EtOAc
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-abbc08c1f2c24e8885abddf908e8cb64
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

反応ノート

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