Triethylamine → HCID 71616876, compound

HRID 930883Notes

Reaction equation

HRID 930883 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.[F:26][C:27]([F:34])([F:33])[CH2:28][S:29](Cl)(=[O:31])=[O:30].C(N(CC)CC)C>ClCCl>[F:26][C:27]([F:34])([F:33])[CH2:28][S:29]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 89657182HCID 89657182, compound

Product 1

HCID 71616876HCID 71616876, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 99b (43.2 mg, 0.127 mmol) in dichloromethane (2 mL) was added 2,2,2-trifluoroethanesulfonyl chloride (0.015 mL, 0.140 mmol) and triethylamine (0.053 mL, 0.382 mmol). The mixture was stirred for 18 hours at ambient temperature. The reaction mixture was concentrated and the residue was purified by flash column chromatography (silica gel, 0.5-5% methanol in dichloromethane) to provide the title compound (20.8 mg, 33.7% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 12.00 (s, 1H), 10.16 (s, 1H), 7.25-7.32 (m, 3H), 7.14-7.20 (m, 2H), 6.18-6.24 (m, 1H), 4.36-4.55 (m, 3H), 3.52-3.68 (m, 5H), 3.33-3.45 (m, 2H), 1.79-1.94 (m, 2H), 1.39-1.57 (m, 2H). MS (ESI+) m/z 486.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash column chromatography (silica gel, 0.5-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ea61a325b04c4915843403b8d52c4ff1
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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