Diisopropylethylamine → HCID 46908501, 화합물

HRID 1694322노트

반응식

HRID 1694322 반응식
[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]([OH:23])=O)([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.[NH2:57][C@@H:58]([C:60]1[CH:71]=[CH:70][C:63]([CH2:64][NH:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[CH:62][CH:61]=1)[CH3:59]>C1COCC1.C(Cl)Cl>[C:66]([NH:65][CH2:64][C:63]1[CH:62]=[CH:61][C:60]([C@H:58]([NH:57][C:21](=[O:23])[CH2:20][CH:12]2[N:11]([S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[CH2:16][CH2:15][N:14]3[CH:17]=[CH:18][CH:19]=[C:13]23)[CH3:59])=[CH:71][CH:70]=1)([CH3:69])([CH3:67])[CH3:68]

참가 물질

7

반응물 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 59486400HCID 59486400, 화합물HCID 59486435HCID 59486435, 화합물

생성물 1

HCID 46908501HCID 46908501, 화합물수율 29%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of 2-(2-tosyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid (S11) (405 mg, 1.2 mmol, 1.0 eq.) in THF (5 ml) were added DIPEA (1.0 ml, 6.0 mmol, 5.0 eq.) and HATU (547 mg, 1.4 mmol, 1.2 eq.) at 0° C. and the mixture was stirred for 15 min at the same temperature. A solution of (R)—N-(4-(1-aminoethyl)-benzyl)-2-methylpropan-2-amine (A54) (1.2 mmol, 1.0 eq.) in THF (3 ml) was added to the reaction mixture and it was stirred at RT for 16 h. The mixture was diluted with DCM (70 ml) and washed with sat. NH4Cl solution (25 ml), sat. NaHCO3 solution (25 ml), water (25 ml) and brine (25 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by column chromatography (silica gel; 3% MeOH/DCM) to yield the desired product as a light brown solid. Yield: 29% (180 mg, 0.334 mmol); MS, Rt=2.9 min; m/z=523.1 [M H]+

후처리

  1. stirringwas stirred at RT for 16 h
  2. washwashed with sat. NH4Cl solution (25 ml), sat. NaHCO3 solution (25 ml), water (25 ml) and brine (25 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product which
  6. customwas purified by column chromatography (silica gel; 3% MeOH/DCM)

출처 및 근거

ORD 기록
ord-c7ce50516892478bb2538c9642d01f09
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158628B2

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