Triethylamine → (4-ethoxy-2-hydroxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

HRID 1908179

反応式

HRID 1908179 の反応式
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([OH:13])[CH:5]=1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:45][N:46]1[C:50]2[C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][C:56]=3[O:57][C:58]3([CH2:63][CH2:62][NH:61][CH2:60][CH2:59]3)[C:49]=2[CH:48]=[N:47]1>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:61]2[CH2:62][CH2:63][C:58]3([C:49]4[CH:48]=[N:47][N:46]([CH3:45])[C:50]=4[C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][C:56]=4[O:57]3)[CH2:59][CH2:60]2)=[O:10])=[C:6]([OH:13])[CH:5]=1)[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 826284-Ethoxysalicylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 585507381-Methylspiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]

生成物 1

HCID 58551483(4-ethoxy-2-hydroxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone収率 32%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

In a vial were added 4-ethoxy-2-hydroxybenzoic acid (0.40 mmol) followed by HATU (170 mg, 0.44 mmol), DMF (0.7 mL), and triethylamine (220 μL, 1.6 mmol). The mixture was stirred for 10 minutes before 1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (100 mg, 0.40 mmol) was added. The reaction mixture was allowed to stir at 25° C. for 12 hours before it was filtered and purified by HPLC (1-99%) MeOH:H2O to yield (4-ethoxy-2-hydroxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (53 mg, 32%). ESI-MS m/z calc. 419.5. found 420.4 (M+1)+. Retention time: 2.96 minutes (4 min run).

後処理

  1. additionwas added
  2. filtrationwas filtered
  3. custompurified by HPLC (1-99%) MeOH

出典と根拠

ORDレコード
ord-b68c4d73b4b2404482827635ae6f885c
出典データセット
uspto-grants-2013_12
特許番号
US08598164B2

関連ノート

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