2,2,2-Trifluoroethanol → HCID 67962991, compound

HRID 1426273Notes

Reaction equation

HRID 1426273 reaction equation
Cl.CN(C)CCCN=C=NCC.[F:13][C:14]([F:18])([F:17])[CH2:15][OH:16].[CH2:19]([N:26]1[CH:30]=[C:29]([CH2:31][C@@H:32]([C:41](O)=[O:42])[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:28]([N+:44]([O-:46])=[O:45])=[N:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:19]([N:26]1[CH:30]=[C:29]([CH2:31][C@@H:32]([C:41]([O:16][CH2:15][C:14]([F:18])([F:17])[F:13])=[O:42])[NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[C:28]([N+:44]([O-:46])=[O:45])=[N:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67962994HCID 67962994, compound

Product 1

HCID 67962991HCID 67962991, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (98%, 361 mg, 1.85 mmol), 4-(dimethylamino)pyridine (97%, 116 mg, 0.921 mmol) and 2,2,2-trifluoroethanol (99%, 1.36 mL, 18.5 mmol) were added to a solution of C7 (0.36 g, 0.92 mmol) in dichloromethane (30 mL), and the reaction mixture was allowed to stir for 18 hours. The reaction was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 100% EtOAc in heptane) afforded C8 as a solid. Yield: 223 mg, 0.472 mmol, 51%. LCMS m/z 471.1 (M−1). 1H NMR (400 MHz, CDCl3) δ 1.37 (s, 9H), 3.24 (br dd, half of ABX pattern, J=14.7, 7.9 Hz, 1H), 3.35 (dd, half of ABX system, J=15.0, 5.7 Hz, 1H), 4.42-4.52 (m, 2H), 4.59 (br ddd, J=8, 8, 6 Hz, 1H), 5.13 (br d, J=8 Hz, 1H), 5.31 (s, 2H), 7.26-7.32 (m, 3H), 7.36-7.42 (m, 3H).

Workup

  1. washThe reaction was washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography (Gradient: 0% to 100% EtOAc in heptane)

Sources & evidence

ORD record
ord-31bc3a3c16194503bb0a9af35b253f90
Source dataset
uspto-grants-2015_01
Patent number
US08933095B2

Reaction notes

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