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Hydrochloric Acid → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(methoxymethyl)thiophene-2-sulfonamide

HRID 1252348
Notes
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Reaction equation

HRID 1252348 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([NH:23][C:24](=O)[O:25]C2C=CC=CC=2)[N:16]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([O:14][CH3:13])[N:16]=[C:17]([NH:23][C:24]([NH:12][S:9]([C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH2:3][O:2][CH3:1])(=[O:11])=[O:10])=[O:25])[N:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 139132183-(Methoxymethyl)thiophene-2-sulfonamide

Product 1

HCID 13913192N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(methoxymethyl)thiophene-2-sulfonamide

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Procedure

To 0.41 g of 3-(methoxymethyl)thiophene-2-sulfonamide and 0.55 g of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate in 20 mL of acetonitrile is added 0.3 mL of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU). After being stirred for 2 hours at ambient temperature and pressure, the reaction mass is poured onto 25-50 g of ice and the resultant mixture acidified to pH 3 by the addition of hydrochloric acid. The desired solid product can be isolated by filtration. Alternatively, it can be extracted into methylene chloride which is then dried over magnesium sulfate, filtered and evaporated to dryness to yield the desired product is sufficiently pure form for the purposes of this invention.

Workup

  1. customThe desired solid product can be isolated by filtration
  2. extractionAlternatively, it can be extracted into methylene chloride which
  3. dry with materialis then dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c1ee071ccd054deabe438b63731c71b7
Source dataset
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04743290

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes