Hydrochloric Acid → HCID 178433743, compound

HRID 1530117Notes

Reaction equation

HRID 1530117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:37])[C:9]2[N:10]=[C:11]([C:27]3[C:28]([CH3:36])=[N:29][N:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=34)[S:12][C:13]=2[C:14]2[N:18]=[CH:17][N:16](COCC[Si](C)(C)C)[N:15]=2)=[CH:4][CH:3]=1.Cl.O1CCOCC1.O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:37])[C:9]2[N:10]=[C:11]([C:27]3[C:28]([CH3:36])=[N:29][N:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=34)[S:12][C:13]=2[C:14]2[NH:18][CH:17]=[N:16][N:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 58094762N-(4-chlorophenyl)-N-methyl-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazol-4-amine

Product 1

HCID 178433743HCID 178433743, compoundYield 84%

Procedure

N-(4-chlorophenyl)-N-methyl-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazol-4-amine (0.0566 g, 0.102 mmol) was treated with 4 M of Hydrochloric acid in 1,4-dioxane (6.0 mL, 24 mmol) and Water (1.0 mL, 56 mmol) at 35° C. to r.t. for 42 hours. The reaction solution was rotavaped, azeotroped with MeOH to give a crude residue. The material was dissolved in small amount of MeOH, diluted with Et2O, filtered to give a solid product. (0.037 g, 84% yield). LCMS: (FA) ES+ 422. 1H NMR (400 MHz, d1-chloroform & d4-methanol) δ 8.89 (0, 1H), 8.41 (d, J=6.78 Hz1-H8.26 (d, J=6.78 Hz, 1H), 7.36 (m, 1H), 7.10-7.12 (d, J=8.78 Hz, 2H), 6.87-6.90 (m, 3H), 3.51 (s, 3H), 2.72 (s, 3H).

Workup

  1. customazeotroped with MeOH

Sources & evidence

ORD record
ord-520f1447cf084e988c27cbffb2e11fc9
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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