Diisopropylethylamine → HCID 59486484、化合物

HRID 1694319ノート

反応式

HRID 1694319 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.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:62][NH:63][CH:64]1[CH2:73][CH2:72][C:71]2[C:66](=[CH:67][CH:68]=[C:69]([CH2:74][N:75]3[CH2:80][CH2:79][CH2:78][CH2:77][CH2:76]3)[CH:70]=2)[CH2:65]1>C1COCC1.C(OCC)(=O)C>[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]([N:63]([CH3:62])[CH:64]1[CH2:73][CH2:72][C:71]3[C:66](=[CH:67][CH:68]=[C:69]([CH2:74][N:75]4[CH2:80][CH2:79][CH2:78][CH2:77][CH2:76]4)[CH:70]=3)[CH2:65]1)=[O:28])(=[O:15])=[O:14])[CH:7]=[CH:6]2

参加物

7

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 59486409HCID 59486409、化合物HCID 594864212-(2-(6-Methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid

生成物 1

HCID 59486484HCID 59486484、化合物収率 47%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-(2-(6-methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo-[1,2-a]pyrazin-1-yl)acetic acid (S2) (200 mg, 0.5 mmol, 1.0 eq.) in THF (6 ml) were added DIPEA (300 μl, 2.0 mmol, 4.0 eq.) and HATU (190 mg, 0.5 mmol, 1.0 eq.) at 0° C. and the resulting mixture was stirred for 15 min at same temperature. A solution of N-methyl-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-amine (A51) (0.6 mmol, 1.2 eq.) in THF (4 ml) was added to the reaction mixture and it was allowed to stir at RT for 16 h. The reaction mixture was diluted with ethyl acetate (30 ml) and washed with sat. NH4Cl solution (20 ml), sat. NaHCO3 solution (20 ml), water (20 ml) and brine (20 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to obtain the crude product which was purified by column chromatography (silica gel; 2-4% MeOH/DCM) to yield the desired product as a white solid. Yield: 47% (150 mg, 0.234 mmol); MS, Rt=3.7 min; m/z=641.1 [MH]+

後処理

  1. stirringto stir at RT for 16 h
  2. washwashed with sat. NH4Cl solution (20 ml), sat. NaHCO3 solution (20 ml), water (20 ml) and brine (20 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the crude product which
  6. customwas purified by column chromatography (silica gel; 2-4% MeOH/DCM)

出典と根拠

ORDレコード
ord-f91e387ec6c14bbab755a0955167463a
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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