Diisopropylethylamine → HCID 73051026, compound

HRID 1048703Notes

Reaction equation

HRID 1048703 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][NH2:21])[CH:6]=[CH:7][CH:8]=1.C(N(C(C)C)CC)(C)C.[CH:33]([S:36](Cl)(=[O:38])=[O:37])([CH3:35])[CH3:34]>ClCCl>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][NH:21][S:36]([CH:33]([CH3:35])[CH3:34])(=[O:38])=[O:37])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 824082-Propanesulfonyl chloride2×HCID 90024362HCID 90024362, compound

Product 1

HCID 73051026HCID 73051026, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.08 g (0.239 mmol) of (3-((3-(trifluoromethyl)phenyl) ethynyl) imidazo[1,2-a]pyridin-2-yl) methanamine (prepared according to steps 1 to 4 of Example 11) were solubilised in 2 ml of dichloromethane with magnetic stirring, 0.208 ml (1.193 mmol) of diisopropylethylamine and 0.083 ml (0.716 mmol) of isopropylsulfonyl chloride were added. The mixture was stirred at r.t. for 16 h. A supplement of 0.083 ml (0.716 mmol) of isopropylsulfonyl chloride was added and the mixture was stirred at r.t. for 1 h before being concentrated in vacuo. The crude residue was directly purified by flash chromatography on a silica gel cartridge (eluent: dichloromethane/methanol 95/5, v/v). 0.048 g (yield=22%) of N-((3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methyl)propane-2-sulfonamide were obtained as a white solid. LC-MS: m/z=422 (MH+); UV purity at 254 nm=98%. 1H NMR (300 MHz, DMSO) δ 8.75 (d, J=6.8 Hz, 1H), 8.13 (s, 1H), 7.99 (d, J=7.5 Hz, 1H), 7.85-7.61 (m, 4H), 7.53-7.38 (m, 1H), 7.15 (t, J=6.8 Hz, 1H), 4.44 (d, J=5.9 Hz, 2H), 3.25 (dd, J=13.6, 6.8 Hz, 1H), 1.21 (d, J=6.8 Hz, 6H).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at r.t. for 1 h
  3. concentrationbefore being concentrated in vacuo
  4. customThe crude residue was directly purified by flash chromatography on a silica gel cartridge (eluent

Sources & evidence

ORD record
ord-1538cf08a9d94142ab0231944dd603b3
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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