Triethylamine → HCID 22280772, compound

HRID 1768108Notes

Reaction equation

HRID 1768108 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[C:6]([C:11]2[CH2:15][C:14]([CH2:20][NH2:21])([C:16]([O:18][CH3:19])=[O:17])[O:13][N:12]=2)[CH:7]=[CH:8][C:9]=1[F:10])#[N:3].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[C:2]([C:4]1[CH:5]=[C:6]([C:11]2[CH2:15][C:14]([CH2:20][NH:21][S:30]([CH3:29])(=[O:32])=[O:31])([C:16]([O:18][CH3:19])=[O:17])[O:13][N:12]=2)[CH:7]=[CH:8][C:9]=1[F:10])#[N:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22280770HCID 22280770, compound

Product 1

HCID 22280772HCID 22280772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3-cyano-4-fluorophenyl)-5-(aminomethyl)-5-(carbomethoxy)isoxazoline hydrochloride salt (1.15 g) in CH2Cl2 (50 mL) was added triethylamine (1.27 mL) and methanesulfonyl chloride (0.31 mL). The mixture was stirred at RT under N2 for 1 h. The solvent was diluted with CH2Cl2 and washed with water, 1N aqueous HCl, and saturated aqueous NaHCO3. It was dried over MgSO4 and concentrated to a yellow solid (1.13 g). 1H NMR (CDCl3) δ 7.92 (m, 2H), 7.30 (t, 1H), 4.82 (t, 1H), 3.84 (s, 3H), 3.76–3.60 (m, 4H), 3.03 (s, 3H) ppm; ESI mass spectrum z (rel. intensity) 377.9 (M+H, 100).

Workup

  1. washwashed with water, 1N aqueous HCl, and saturated aqueous NaHCO3
  2. dry with materialIt was dried over MgSO4
  3. concentrationconcentrated to a yellow solid (1.13 g)

Sources & evidence

ORD record
ord-7bc482fb5dcf4a75955166291daf7d78
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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