Triethylamine → Ammonium Acetate

HRID 1469936

반응식

HRID 1469936 반응식
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[S:11][C:10](=[NH:12])[N:9]([CH2:13][CH2:14][O:15][CH3:16])[CH:8]=2)=[CH:4][CH:3]=1.[CH2:19]1[CH:26]2[C:22]3([C:28]([OH:30])=[O:29])[CH2:23][CH:24]([CH2:27][CH:20]1[CH2:21]3)[CH2:25]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[C:28]([O-:30])(=[O:29])[CH3:22].[NH4+:9].[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[S:11][C:10](=[N:12][C:28]([C:22]34[CH2:23][CH:24]5[CH2:27][CH:20]([CH2:19][CH:26]3[CH2:25]5)[CH2:21]4)=[O:29])[N:9]([CH2:13][CH2:14][O:15][CH3:16])[CH:8]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668590705-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene-amine

생성물 2

HCID 517165Ammonium AcetateHCID 24890079HCID 24890079, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of the product of Example 43A (342 mg, 1.29 mmol), hexahydro-2,5-methano-pentalene-3a-carboxylic acid (256 mg, 1.54 mmol), HATU (737 mg, 1.24 mmol) and triethylamine (1.08 mL, 7.74 mmol) in 20 mL of DMF was stirred at room temperature for overnight. The mixture was diluted with ethyl acetate and washed with water. The organic extract was dried (MgSO4), filtered and concentrated. The residue was purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes to afford the title compound: 1H NMR (500 MHz, DMSO-d6) δ 1.51-1.61 (m, 4H) 1.64-1.75 (m, 4H) 2.06 (d, J=9.2 Hz, 2H) 2.22-2.27 (m, 2H) 2.51-2.53 (m, 1H) 3.25 (s, 3H) 3.67 (t, J=5.3 Hz, 2H) 3.95 (s, 2H) 4.23 (t, J=5.2 Hz, 2H) 7.15 (t, J=8.8 Hz, 2H) 7.23 (s, 1H) 7.29 (dd, J=8.4, 5.6 Hz, 2H); MS (DCI/NH3) m/z 415 (M+H)+.

후처리

  1. washwashed with water
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)

출처 및 근거

ORD 기록
ord-5eb2b9baa88c464283358faed46f0019
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006275B2

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