Diisopropylethylamine → HCID 46909184、化合物

HRID 1694316ノート

反応式

HRID 1694316 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]3[CH:22]=[CH:23][CH:24]=[C:18]3[CH:17]1[CH2:25][C:26]([OH:28])=O)(=[O:15])=[O:14])[CH:7]=[CH:6]2.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.[C:62]([NH:66][CH2:67][C:68]1[CH:69]=[C:70]2[C:75](=[CH:76][CH:77]=1)[CH2:74][CH:73]([NH2:78])[CH2:72][CH2:71]2)([CH3:65])([CH3:64])[CH3:63]>C(Cl)Cl>[C:62]([NH:66][CH2:67][C:68]1[CH:69]=[C:70]2[C:75](=[CH:76][CH:77]=1)[CH2:74][CH:73]([NH:78][C:26](=[O:28])[CH2:25][CH:17]1[N:16]([S:13]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]=3)(=[O:14])=[O:15])[CH2:21][CH2:20][N:19]3[CH:22]=[CH:23][CH:24]=[C:18]13)[CH2:72][CH2:71]2)([CH3:65])([CH3:63])[CH3:64]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594864212-(2-(6-Methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acidHCID 59486444HCID 59486444、化合物

生成物 1

HCID 46909184HCID 46909184、化合物収率 34%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a cooled (0° C.) suspension of 2-(2-(6-methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid (S2) (310 mg, 0.77 mmol, 1.0 eq.) in DCM (20 ml) was added HATU (600 mg, 1.54 mmol, 2 eq.) and DIPEA (0.4 ml, 2.31 mmol, 3 eq.) and the reaction mixture was allowed to stir for 30 min. Finally, 6-((tert-Butylamino)methyl)-1,2,3,4-tetrahydronaphthalen-2-amine (A15) (180 mg, 0.77 mmol, 1.0 eq.) was added and the reaction mixture and it was stirred at RT for 16 h. The mixture was diluted with DCM (100 ml) and successively washed with ammonium chloride solution (50 ml), sodium bicarbonate solution (50 ml), water (10 ml) and brine (10 ml). The organics were dried over Na2SO4 and the solvent was evaporated under reduced pressure to give the crude product which was purified by column chromatography (silica gel, 6% MeOH/DCM) to yield the pure title compound as a white solid. Yield: 34% (160 mg, 0.26 mmol); MS, Rt=3.6 min; m/z=615.1 [MH]+

後処理

  1. temperatureTo a cooled
  2. stirringthe reaction mixture and it was stirred at RT for 16 h
  3. washsuccessively washed with ammonium chloride solution (50 ml), sodium bicarbonate solution (50 ml), water (10 ml) and brine (10 ml)
  4. dry with materialThe organics were dried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customto give the crude product which
  7. customwas purified by column chromatography (silica gel, 6% MeOH/DCM)

出典と根拠

ORDレコード
ord-0d809fd21b3446dfa74c21ae09aaaa15
出典データセット
uspto-grants-2012_04
特許番号
US08158628B2

反応ノート

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