3-Methylbenzoic acid → N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-3-methylbenzamide

HRID 42255

反応式

HRID 42255 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:44]1[C:52]2[C:47](=[C:48]([C:53]3[CH:54]=[C:55]([NH2:62])[C:56]4[CH:57]=[N:58][NH:59][C:60]=4[CH:61]=3)[CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45]1>CN(C=O)C>[NH:44]1[C:52]2[C:47](=[C:48]([C:53]3[CH:61]=[C:60]4[C:56]([CH:57]=[N:58][NH:59]4)=[C:55]([NH:62][C:5](=[O:7])[C:4]4[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=4)[CH:54]=3)[CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45]1

参加物

6

反応物 4

HCID 74183-Methylbenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

生成物 1

HCID 44540402N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-3-methylbenzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

3-Methylbenzoic acid (60 mg, 0.44 mmol) was treated with HATU (168 mg, 0.44 mmol) in DMF (0.750 mL) and DIPEA (0.15 mL, 0.86 mmol). The mixture was shaken for five minutes prior to treatment with 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.2 mmol) in DMF (0.350 mL) and was then left to stand at room temperature for 16 hrs. Solvent was removed in vacuo and the product re-dissolved in chloroform (0.3 mL) prior to application on to a pre-conditioned (methanol then chloroform) NH2 cartridge (1 g). Product was eluted after 2 hr with ethyl acetate/methanol (1:1, 3.2 mL), and concentrated under a stream of nitrogen using blow down apparatus. Purification by MDAP (Method C) afforded the title compound.

後処理

  1. waitto stand at room temperature for 16 hrs
  2. customSolvent was removed in vacuo
  3. dissolutionthe product re-dissolved in chloroform (0.3 mL)
  4. washProduct was eluted after 2 hr with ethyl acetate/methanol (1:1, 3.2 mL)
  5. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  6. customPurification by MDAP (Method C)

出典と根拠

ORDレコード
ord-0f9fc47f8c304901be6b41edb9604a18
出典データセット
uspto-grants-2013_09
特許番号
US08536169B2

関連ノート

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