3-chloro-N-methylpropan-1-amine → HCID 68512753, compound

HRID 1716314Notes

Reaction equation

HRID 1716314 reaction equation
[CH3:1][O:2][C:3]([C@H:5](OS(C(F)(F)F)(=O)=O)[CH2:6][N:7]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[S:8]([CH3:11])(=[O:10])=[O:9])=[O:4].[CH3:37][NH:38][CH2:39][CH2:40][CH2:41][Cl:42]>C(Cl)Cl>[Cl:42][CH2:41][CH2:40][CH2:39][N:38]([C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)[S:8]([CH3:11])(=[O:9])=[O:10])[CH3:37]

Participants

4

Reactant 2

HCID 5418743-chloro-N-methylpropan-1-amineHCID 59704783HCID 59704783, compound

Product 1

HCID 68512753HCID 68512753, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(2R)-2-methoxycarbonyl-2-trifluoromethanesulfonyloxyethyl]-N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (565 mg, 1.0 mmol) from Step C in dried CH2Cl2 (2 mL) at 0° C. under N2 was added N-methyl-3-chloropropyl-amine (ca. 1.0 M in CH2Cl2, 4.0 mL, 4.0 mmol) dropwise. The mixture was allowed to warm to room temperature and was stirred for 1 h. The mixture was directly concentrated to give a crude mixture, which was purified by silica gel chromatography using EtOAc/hexane (1/4 to 1/1) as the eluent to give 455 mg of the product (81%) as a sticky oil. 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J=9.0 Hz, 2H), 7.35 (d, J=9.0 Hz, 2H), 7.12-7.04 (m, 4H), 3.96-3.90 (m, 2H), 3.69 (s, 3H), 3.59-3.54 (m, 2H), 3.47 (t, J=7.5 Hz, 1H), 2.94 (s, 3H), 2.75-2.55 (m 2H), 2.27 (s, 3H), 1.90-1.83 (m, 2H); MS (EI) 522 (M++1, 100).

Workup

  1. concentrationThe mixture was directly concentrated
  2. customto give a crude mixture, which
  3. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-6a301509771548c7aca624497596e393
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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