Triethylamine → HCID 19850838, compound

HRID 1607564Notes

Reaction equation

HRID 1607564 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][S:10]([C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][NH:19][CH2:20]3)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39]Br>C(#N)C>[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][N:19]1[CH2:18][CH2:17][C:16]2[C:21](=[CH:22][C:13]([S:10](=[O:12])(=[O:11])[NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=3)=[CH:14][CH:15]=2)[CH2:20]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 2734813Methyl 2-(bromomethyl)benzoateHCID 12606941HCID 12606941, compound

Product 1

HCID 19850838HCID 19850838, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

To a mixture of 7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.8 g, 5 mmol) and triethylamine (0.51 g, 5 mmol) in dry acetonitrile (25 ml), heated to 70° C., was added half of a solution of methyl-2-(bromomethyl)benzoate (1.15 g, 5 mmol) and triethylamine (0.51 g, 5 mmol) in acetonitrile (25 ml) over 0.5 hr. After 1.5 hr, the remainder of the solution was added slowly over 2 hr and stirred for a further 1 hr. After cooling and filtration the concentrated filtrate was chromatographed (silica gel, ether) to give a methyl-2-[[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methyl]benzoate (0.66 g, 28%) as an oil. To this, in methanol (30 ml), was added 15% sodium hydroxide solution (8 ml) and the mixture was stirred for 3 hr. The solvent was removed in vacuo, water was added and the pH was adjusted to 6 with 2N HCl to give, after recrystallisation from IPA, 2-[[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methyl]benzoic acid, H2O, 0.6HCl, 0.48(CH3)2CHOH.

Workup

  1. additionthe remainder of the solution was added slowly over 2 hr
  2. temperatureAfter cooling
  3. filtrationfiltration the concentrated filtrate
  4. customwas chromatographed (silica gel, ether)

Sources & evidence

ORD record
ord-bbcbade1ed054561b6539462ec217514
Source dataset
uspto-grants-1989_09
Patent number
US04866076

Reaction notes

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