Lithium hydroxide, monohydrate → 4-[5-(1-Oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid

HRID 552394Notes

Reaction equation

HRID 552394 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[N:13]([CH:27]=[CH:28][N:29]=3)[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[NH:21][CH2:20]4)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1.ClC1N2C=CN=C2C(NC2C=CC(N3CCN(C(C)C)CC3)=CC=2)=CC=1.O.[OH-].[Li+]>CCO.CCOC(C)=O>[O:26]=[C:22]1[C:23]2[C:19](=[CH:18][C:17]([C:14]3[N:13]4[CH:27]=[CH:28][N:29]=[C:12]4[C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[CH:5][CH:6]=4)=[CH:16][CH:15]=3)=[CH:25][CH:24]=2)[CH2:20][NH:21]1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 57580685HCID 57580685, compoundHCID 57580808(5-Chloro-imidazo[1,2-a]pyridin-8-yl)-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amine

Product 1

HCID 575806954-[5-(1-Oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

Crude 4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid methyl ester (500 mg, 1.256 mmol), prepared using methods similar to those described for compound 12, and lithium hydroxide hydrate (263.5 mg, 6.281 mmol) in solution in THF/water (1/1: 10 mL) is stirred at room temperature for 36 hours then heated 4 hours at 60° C. The mixture is concentrated and then acidified to pH 1 with aqueous 2N HCl. The resulting precipitate is filtrated to yield the title compound, which is used as such for the next step.

Workup

  1. temperaturethen heated 4 hours at 60° C
  2. concentrationThe mixture is concentrated
  3. filtrationThe resulting precipitate is filtrated

Sources & evidence

ORD record
ord-a9c704cb23c04780bfbb2e5299d7f66a
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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