Tetrahydrofuran → HCID 71201935, compound

HRID 1908683Notes

Reaction equation

HRID 1908683 reaction equation
Cl.CN(C)CCCN=C=NCC.ON1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.Cl.[NH2:24][C@H:25]([C:28]1[CH:29]=[N:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=1)[CH2:26][OH:27].C(N(CC)C(C)C)(C)C.[CH2:47]1[CH2:51][O:50][CH2:49][CH2:48]1>O>[OH:27][CH2:26][C@H:25]([NH:24][C:49]([C@H:48]1[CH2:47][C@@H:51]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:50])[C:28]1[CH:29]=[N:30][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71182945HCID 71182945, compound

Product 1

HCID 71201935HCID 71201935, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.39 g, 2.03 mmol) and 1-hydroxybenzotriazole (0.366 g, 2.71 mmol) were added to a stirred mixture of IM46 (0.22 g, 1.36 mmol) and commercially available (R)-2-amino-2-(6-trifluoromethyl-pyridin-3-yl)-ethanol hydrochloride (Supplier Netchem Inc., Catalog No 517882) (0.494 g, 2.03 mmol) and N,N-diisopropylethylamine (0.472 ml, 2.71 mmol) in THF (20 ml). The solution was stirred at rt overnight. Water was added and the mixture was extracted with EtOAc (3×80 ml). The combined organic phases were washed with brine, dried over MgSO4, filtered and the solvent was evaporated of in vac. The crude product was purified by silica gel chromatography (EtOAc in heptanes 10:1). Yield of Compound 22475 mg (78%). 1H-NMR (500 MHz, DMSO) δ 8.77 (d, 1H), 8.74 (s, 1H), 8.00 (d, 1H), 7.88 (d, 1H), 7.27 (m, 2H), 7.18 (m, 1H), 7.13 (d, 2H), 5.04 (m, 2H), 3.64 (m, 2H), 2.22 (m, 1H), 2.07 (m, 1H), 1.37 (m, 1H), 1.37 (m, 1H), 1.23 (m, 1H). LC-MS (m/z) 351.1 (MH+), tR=1.51 min (method A).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×80 ml)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated of in vac
  6. customThe crude product was purified by silica gel chromatography (EtOAc in heptanes 10:1)

Sources & evidence

ORD record
ord-e607f9737dd849de9da14fa405eee059
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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