Acetic Acid → HCID 18327665, compound

HRID 1250404Notes

Reaction equation

HRID 1250404 reaction equation
[CH3:1][N:2]([CH3:40])[C:3]1[CH:39]=[CH:38][C:6]([CH2:7][NH:8][C:9]([C:11]2[N:12]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35](=S)[NH2:36])[CH:30]=3)[C:13]3[C:18]([CH:19]=2)=[C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=[CH:15][CH:14]=3)=[O:10])=[CH:5][CH:4]=1.C[I:42].[C:43](O)(=O)C.C([O-])(=O)C.[NH4+:51]>CC(C)=O.CO>[IH:42].[I-:42].[C:35]([C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=1)[CH2:28][N:12]1[C:13]2[C:18](=[C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:11]1[C:9]([NH:8][CH2:7][C:6]1[CH:38]=[CH:39][C:3]([N+:2]([CH3:40])([CH3:43])[CH3:1])=[CH:4][CH:5]=1)=[O:10])(=[NH:36])[NH2:51]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 53978782HCID 53978782, compound

Product 1

HCID 18327665HCID 18327665, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 887MethanolSolvent

Procedure

This compound was prepared from 4-benzyloxy-1-(3-thiocarbamoyl-benzyl)-1H-indole-2-carboxylic acid 4-(dimethylamino)-benzylamide (342 mg, 0.62 mmol), acetone (15 ml), methyl iodide (0.98 ml, 15 mmol), acetic acid (0.4 m, 0.7 mmol), ammonium acetate (809 mg, 10 mmol), and methanol (7 ml) as described in example 1/5 but the solvent for the methylation was pure acetone. The crude material was purified by flash chromatography on RP18 material with ethanol/water/acetic acid 1:1:0.1 to give 374 mg of the desired compound (80 %). M.p. 158° C. (dec.). MS: 546.2 (M+).

Workup

  1. customThe crude material was purified by flash chromatography on RP18 material with ethanol/water/acetic acid 1:1:0.1

Sources & evidence

ORD record
ord-a0d34b4b13d64901816486ab78eb7e84
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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