Hydrochloric Acid → HCID 178484435, compound

HRID 1792602Notes

Reaction equation

HRID 1792602 reaction equation
[CH3:1][N:2]([CH3:48])[C:3]([C:5]1[S:6][C:7]([C:10]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([C:24]5[S:25][CH:26]=[CH:27][N:28]=5)=[CH:22][N:23]=4)[CH:20]=3)=[CH:13][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=2)=[CH:8][CH:9]=1)=[O:4].[ClH:49]>O1CCCC1.CO>[ClH:49].[ClH:49].[CH3:1][N:2]([CH3:48])[C:3]([C:5]1[S:6][C:7]([C:10]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([C:24]5[S:25][CH:26]=[CH:27][N:28]=5)=[CH:22][N:23]=4)[CH:20]=3)=[CH:13][NH:12][N:11]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23537798HCID 23537798, compound

Product 1

HCID 178484435HCID 178484435, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

29 mg 5-[4-(3-thiazol-2-yl-imidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]-thiophen-2-carboxylic acid dimethylamide obtained in Example 444 was dissolved in 8.0 mL solvent mixture of tetrahydrofuran and methanol (1:1), then 3.0 mL of 5 N hydrochloric acid was added thereto, and the mixture was left at room temperature for 3 hours. The reaction solution was neutralized, then extracted with ethyl acetate and purified by NH silica gel column chromatography (ethyl acetate/hexane) The product was converted into the corresponding hydrochloride by 4 N hydrogen chloride in ethyl acetate and recrystallized from methanol/ethyl acetate to give 20 mg of the title compound as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. custompurified by NH silica gel column chromatography (ethyl acetate/hexane) The product
  3. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-52cb38bd3ddb48daa42adc147a36af6f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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