Ammonia → HCID 18325152, compound

HRID 1250950Notes

Reaction equation

HRID 1250950 reaction equation
N.C[N:3]([CH:5]=[O:6])C.[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:17]([CH3:32])=[C:18](C(O)=O)[CH:19]=[C:20]4[C:28]=3[C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=[CH:21]4)=[CH:15][C:10]=2[O:9][CH2:8]1>O>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:17]([CH3:32])=[C:18]([C:5]([NH2:3])=[O:6])[CH:19]=[C:20]4[C:28]=3[C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=[CH:21]4)=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 4931639-(1,3-Benzodioxol-5-yl)-8-methyl-benzo[g][1,3]benzodioxole-7-carboxylic acid

Product 1

HCID 18325152HCID 18325152, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

WSC[1-Ethyl-3-(3-dimethylaminopropyl) carbodimide hydrochloride](33 mg) and ammonia (3N ethanol solution:0.14 ml) were added under ice-cooling to a DMF solution of 9-(1,3-benzodioxole-5yl)-8-methyl-naphtho[1,2-d]-1,3,-dioxole-7-carboxylic acid (50 mg) which was prepared in Reference Example 13. The mixture was stirred at room temperature for 2 hours, and the reaction was stopped with addition of water. The residue was purified with column chromatography (Silica-Gel 5 g, eluent:ethyl acetate-hexane=1:1) and recrystalized from methanol to yield the title compound (23 g).

Workup

  1. customwas prepared in Reference Example 13
  2. customThe residue was purified with column chromatography (Silica-Gel 5 g, eluent:ethyl acetate-hexane=1:1)
  3. customrecrystalized from methanol

Sources & evidence

ORD record
ord-cf8400b3e4b0451e8cf7008b883f055a
Source dataset
uspto-grants-2002_01
Patent number
US06340704B1

Reaction notes

Loading…