1,4-Dioxane hydrochloride → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3-thiazole-5-carboxylic acid

HRID 2234010Notes

Reaction equation

HRID 2234010 reaction equation
[C:1]([C:4]1[CH:38]=[CH:37][CH:36]=[CH:35][C:5]=1[C:6]([NH:8][CH2:9][C:10]1[N:11]=[C:12]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]([C:27]3[NH:28][C:29]([CH3:34])=[C:30]([Cl:33])[C:31]=3[Cl:32])=[O:26])[CH2:20][CH2:19]2)[S:13][C:14]=1[C:15]([OH:17])=[O:16])=[O:7])([OH:3])=O.Cl.O1CCOCC1>>[Cl:32][C:31]1[C:30]([Cl:33])=[C:29]([CH3:34])[NH:28][C:27]=1[C:25]([NH:24][CH:21]1[CH2:22][CH2:23][N:18]([C:12]2[S:13][C:14]([C:15]([OH:17])=[O:16])=[C:10]([CH2:9][N:8]3[C:6](=[O:7])[C:5]4[C:4](=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:1]3=[O:3])[N:11]=2)[CH2:19][CH2:20]1)=[O:26]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68581174HCID 68581174, compound

Product 1

HCID 685796992-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3-thiazole-5-carboxylic acidYield 32.4%

Procedure

4-{[(2-Carboxybenzoyl)amino]methyl}-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylic acid (Example 244; 100 mg; 0.17 mmol) was stirred with 4 N HCl/Dioxane (3 ml) at room temperature for 8 h. The mixture was concentrated in vacuo and the resulting solid was purified by reversed phase HPLC eluting with water/acetonitrile/ammonium acetate buffer mixtures giving the title compound (31 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting solid was purified by reversed phase HPLC
  3. washeluting with water/acetonitrile/ammonium acetate buffer mixtures

Sources & evidence

ORD record
ord-fa7f709dd7a04f43aad1666b558fafd6
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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