Phthalic Acid → HCID 15228548, compound

HRID 1609482Notes

Reaction equation

HRID 1609482 reaction equation
[C:1]([OH:12])(=O)[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=[O:5].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:29]3[CH2:28][C@@H:27]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])[N:26]([C:35](=[O:49])[CH:36]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:25][C:24]=3[N:23]=[CH:22]2)=[CH:16][C:15]=1[CH3:50]>C(OCC)(=O)C>[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:29]3[CH2:28][C@@H:27]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])[N:26]([C:35](=[O:49])[CH:36]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:25][C:24]=3[N:23]=[CH:22]2)=[CH:16][C:15]=1[CH3:50])=[O:12])([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 1017Phthalic AcidHCID 15228557HCID 15228557, compound

Product 1

HCID 15228548HCID 15228548, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of phthalic acid (0.7223 g, 0.00435 mol) in ethyl acetate (10 ml) was added to a solution of (S)-1-(4-amino-3-methylphenyl)methyl-N,N-dimethyl-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo-[4,5-c]pyridine-6-carboxamide (II-2) (2.0077 g, 0.00396 mol) in ethyl acetate (30 ml) with stirring at room temperature. The mixture was stirred at room temperature for 23 hours, followed by filtration of the reaction mixture. The resulting white solid was washed with ethyl acetate (about 20 ml) and dried to obtain the objective compound (I-2, Compound No. 2) (2.4107 g; yield: 93.0%). MS 637 (EI): (M-18).

Workup

  1. stirringThe mixture was stirred at room temperature for 23 hours
  2. filtrationfollowed by filtration of the reaction mixture
  3. washThe resulting white solid was washed with ethyl acetate (about 20 ml)
  4. customdried
  5. customto obtain the objective compound (I-2, Compound No. 2) (2.4107 g; yield: 93.0%)

Sources & evidence

ORD record
ord-af886fcb67ad46399b825172e1ad23d1
Source dataset
uspto-grants-1995_03
Patent number
US05401736

Reaction notes

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