Diisopropylethylamine → N-[(1R)-6-[(tert-Butylamino)-methyl]-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[2-(p-tolylsulfonyl)-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrazin-1-yl]-acetamide

HRID 1694318ノート

反応式

HRID 1694318 の反応式
[S:1]([N:11]1[CH2:16][CH2:15][N:14]2[CH:17]=[CH:18][CH:19]=[C:13]2[CH:12]1[CH2:20][C:21](O)=[O:22])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O: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.[C:57]([NH:61][CH2:62][C:63]1[CH:64]=[C:65]2[C:70](=[CH:71][CH:72]=1)[C@H:69]([NH2:73])[CH2:68][CH2:67][CH2:66]2)([CH3:60])([CH3:59])[CH3:58]>C1COCC1.C(OCC)(=O)C>[C:57]([NH:61][CH2:62][C:63]1[CH:64]=[C:65]2[C:70](=[CH:71][CH:72]=1)[C@H:69]([NH:73][C:21](=[O:22])[CH2:20][CH:12]1[N:11]([S:1]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=3)(=[O:2])=[O:3])[CH2:16][CH2:15][N:14]3[CH:17]=[CH:18][CH:19]=[C:13]13)[CH2:68][CH2:67][CH2:66]2)([CH3:60])([CH3:58])[CH3:59]

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 58645992(R)-6-((tert-butylamino)methyl)-1,2,3,4-tetrahydronaphthalen-1-amineHCID 59486400HCID 59486400、化合物

生成物 1

HCID 46908411N-[(1R)-6-[(tert-Butylamino)-methyl]-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[2-(p-tolylsulfonyl)-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrazin-1-yl]-acetamide収率 19%

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-tosyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid (S11) (300 mg, 0.898 mmol, 1.0 eq.) in THF (5 ml) were added DIPEA (0.47 ml, 2.694 mmol, 3.0 eq.) and HATU (410 mg, 1.08 mmol, 1.2 eq.) at 0° C. and the mixture was stirred for 15 min at the same temperature. A solution of (R)-6-((tert-butylamino)methyl)-1,2,3,4-tetrahydronaphthalen-1-amine (A50) (0.898 mmol, 1.0 eq.) in THF (5 ml) was added to the reaction mixture and it was stirred at RT for 16 h. The reaction mixture was diluted with ethyl acetate (50 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 get the crude product which was purified by column chromatography (silica gel; 1.5% MeOH/DCM) to yield the desired product as an off-white solid. Yield: 19% (94 mg, 0.171 mmol); MS, Rt=3.2 min; m/z=549.1 [MH]+

後処理

  1. stirringwas stirred 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 get the crude product which
  6. customwas purified by column chromatography (silica gel; 1.5% MeOH/DCM)

出典と根拠

ORDレコード
ord-5cf70bbac4d74f66aebe469e63601bb6
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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