3,4-Diaminobenzoic acid → HCID 178498161, compound

HRID 2284103Notes

Reaction equation

HRID 2284103 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([C:22]([OH:24])=O)=[CH:21][C:15]=4[N:14]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.O1CCN(C2C=CC(C=O)=CC=2)C[CH2:26]1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].N[C:49]1[CH:50]=[C:51]([CH:55]=[CH:56][C:57]=1[NH2:58])[C:52]([OH:54])=[O:53]>O.CC(O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([C:22]([NH:58][C:57]5[CH:56]=[CH:55][C:51]([C:52]([O:54][CH3:26])=[O:53])=[CH:50][CH:49]=5)=[O:24])=[CH:21][C:15]=4[N:14]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 692633,4-Diaminobenzoic acidHCID 2913494-MorpholinobenzaldehydeHCID 656671Sodium PyrosulfiteHCID 178524157HCID 178524157, compound

Product 1

HCID 178498161HCID 178498161, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Compound 167 was prepared according to the general procedure similar to that described in Scheme III. Preparation of 2-(4-morpholinophenyl)-1H-benzo[d]imidazole-5-carboxylic acid: 4-Morpholinobenzaldehyde (475 mg, 2.5 mmole), sodium metabisulfite (85 mg) and 3,4-diaminobenzoic acid (152 mg, 2.7 mmole) were placed in a 10-mL microwave tube and 5.0 mL HPLC grade 2-propanol added. The reaction mixture was microwaved at 170° C. for 55 minutes. The reaction mixture was added dropwise to 25 mL water and stirred at room temperature for 30 min. then it was filtered and washed with plenty of water, ethyl acetate and hexanes and dried to provide the pure intermediate acid (323 mg, 40% yield). This compound was used for next step without any further purification.

Workup

  1. customThe reaction mixture was microwaved at 170° C. for 55 minutes
  2. filtrationit was filtered
  3. washwashed with plenty of water, ethyl acetate and hexanes
  4. customdried

Sources & evidence

ORD record
ord-4b60ad84cb1d45b79aaf996c6abda851
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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