Diisopropylethylamine → HCID 46221496, 화합물

HRID 1094781

반응식

HRID 1094781 반응식
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[C:5]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[C@H:47]12[CH2:53][C@H:52]1[CH2:51][C@@H:50]([CH2:54][NH:55][C:56]1[CH:61]=[N:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][N:57]=1)[NH:49][CH2:48]2.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([N:49]2[C@H:50]([CH2:54][NH:55][C:56]3[CH:61]=[N:60][C:59]([C:62]([F:65])([F:63])[F:64])=[CH:58][N:57]=3)[CH2:51][C@H:52]3[C@H:47]([CH2:53]3)[CH2:48]2)=[O:10])[C:5]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 593637336-methyl-3-(2H-1,2,3-triazol-2-yl)picolinic acidHCID 59396007N-[(1S,4S,6S)-3-azabicyclo[4.1.0]hept-4-ylmethyl]-5-(trifluoromethyl)-2-pyrazinamine

생성물 1

HCID 46221496HCID 46221496, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

6-methyl-3-(2H-1,2,3-triazol-2-yl)-2-pyridinecarboxylic acid D40 (33.0 mg) was dissolved in 1 ml of DCM, then TBTU (61.3 mg, 0.191 mmol) and DIPEA (0.033 ml, 0.191 mmol) were added. The suspension was stirred for 30 minutes at room temperature. N-[(1S,4S,6S)-3-azabicyclo[4.1.0]hept-4-ylmethyl]-5-(trifluoromethyl)-2-pyrazinamine D31 (40 mg) dissolved in 1 ml of DCM was added and the reaction was stirred overnight at room temperature. 3 ml of NaHCO3 saturated solution were added, and the aqueous layer was extracted with DCM. The organic layers were collected together, dried through a phase separator and concentrated under vacuum to give a crude which was purified by SCX chromatography (column size 5 g). A second purification was performed by Silica —NH chromatography (Biotage SP—column size 25 g, using Cy:EtOAc=5:5 to EtOAc). It was recovered the title compound E6 (30 mg). UPLC: (Acid Final_QC): rt=0.76 and 0.80 minutes (rotamers present), peaks observed: 459 (M+1). C21H21F3N8O requires 458. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.38 (s, 1 H) 8.28-8.22 (m, 1 H) 8.08-8.06 (s, 2 H), 7.90-7.78 (m, 2 H), 7.57-7.51 (m, 1 H) 4.20-4.08 (m, 1 H) 3.76-3.40 (m, 3 H), 2.68-2.61 (m, 1 H), 2.56 (s, 3 H), 2.44-2.35 (m, 1 H), 1.28-0.95 (m, 2 H), 0.92-0.83 (m, 1 H), 0.68-0.60 (m, 1 H), 0.24-0.18 (m, 1 H).

후처리

  1. additionwas added
  2. stirringthe reaction was stirred overnight at room temperature
  3. extractionthe aqueous layer was extracted with DCM
  4. customThe organic layers were collected together
  5. customdried through a phase separator
  6. concentrationconcentrated under vacuum
  7. customto give a crude which
  8. customwas purified by SCX chromatography (column size 5 g)
  9. customA second purification
  10. customIt was recovered the title compound E6 (30 mg)
  11. customrt=0.76 and 0.80 minutes (rotamers present)

출처 및 근거

ORD 기록
ord-a945bddd27e84642a23adfeb52a2abab
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133908B2

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