Methylamine → HCID 59446523, compound

HRID 1510312Notes

Reaction equation

HRID 1510312 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:31]([N:34]([CH2:38]C)C(C)C)(C)C.C(Cl)(Cl)=[O:41].CN>ClCCl.C1(C)C=CC=CC=1.O1CCCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][P:23](=[O:30])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:38](=[O:41])[NH:34][CH3:31])[CH2:17][CH2:16]3)(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

9

Reactant 4

HCID 6329MethylamineHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 59446513HCID 59446513, compound

Product 1

HCID 59446523HCID 59446523, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1.27 g diethyl {[(3,5-dichloro-phenylsulphonyl)-(2,3-dihydro-1H-indol-5-yl)-amino]-methyl}-phosphonate are dissolved in 10 ml dichloromethane and cooled to 0° C. To this are added 410 μl N,N-diisopropyl-ethylamine and 6.8 ml of a 20% solution of phosgene in toluene. The mixture is left for 1 hour with stirring and then the solvents are eliminated in a nitrogen current. The residue is taken up in 40 ml of tetrahydrofuran, 6.45 ml of a 2 M solution of methylamine in tetrahydrofuran are added and the mixture is stirred overnight at ambient temperature. Then it is diluted with dichloromethane and 1 N hydrochloric acid and washed with semisaturated sodium chloride solution. The organic phase is dried on magnesium sulphate, the solvents are eliminated in vacuo and the residue is purified by chromatography on silica gel (dichloromethane/methanol 95:5 to 60:40).

Workup

  1. stirringthe mixture is stirred overnight at ambient temperature
  2. washwashed with semisaturated sodium chloride solution
  3. customThe organic phase is dried on magnesium sulphate
  4. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 95:5 to 60:40)

Sources & evidence

ORD record
ord-3786dddf116c4f829e22b82a14ee56d0
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

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