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1,4-Dioxane hydrochloride → N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride

HRID 1184839
Notes
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Reaction equation

HRID 1184839 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[CH:4][C:3]=1[NH:16][C:17]([C:19]1[S:27][C:22]2=[N:23][CH:24]=[CH:25][N:26]=[C:21]2[CH:20]=1)=[O:18].[ClH:28].O1CCOCC1>O1CCOCC1>[ClH:28].[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:16][C:17]([C:19]2[S:27][C:22]3=[N:23][CH:24]=[CH:25][N:26]=[C:21]3[CH:20]=2)=[O:18])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67125544Tert-butyl 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)phenylcarbamate

Product 1

HCID 67125547N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)phenylcarbamate 28 (5.36 g, 13.94 mmol) in dioxane (20 mL) was added 4N HCl/Dioxane (8.71 mL, 34.9 mmol). The reaction was stirred overnight at 60° C. Evaporated to dryness to give N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride 29 (4.47 g, 100%). NMR (400 MHz, DMSO-d6) 2.32 (s, 3H), 7.25 (dd, J=8.2 and 2.3 Hz, 1H), 7.44 (d, J=8.6 Hz, 1H), 7.49 (d, J=1.9 Hz, 1H), 8.65 (s, 1H), 8.77 (d, J=2.3 Hz, 1H), 8.90 (d, J=2.3 Hz, 1H), 10.3 (br s, 2H), 10.70 (s, 1H).

Workup

  1. customEvaporated to dryness

Sources & evidence

ORD record
ord-3dcc055c838a4ab385cd6fa7a422d4d4
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669256B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes