Sodium Hydroxide → HCID 140606265, compound

HRID 1631541Notes

Reaction equation

HRID 1631541 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH3:8][S:9][C:10](=[NH:12])[NH2:11].[NH2:13][C:14]1[C:15]([C:26](OC(C)=CC(=O)NC(C)(C)C)=[O:27])=[N:16][C:17]([Cl:25])=[C:18]([NH:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[N:19]=1>C1COCC1>[NH2:13][C:14]1[C:15]([C:26]([NH:12][C:10]([S:9][CH3:8])=[NH:11])=[O:27])=[N:16][C:17]([Cl:25])=[C:18]([NH:20][CH2:21][CH:22]2[CH2:23][CH2:24]2)[N:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 86682676HCID 86682676, compound

Product 1

HCID 140606265HCID 140606265, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To NaOH (2 mol/l in water; 9.07 ml; 18.1 mmol) is added S-methylisothiourea sulphate (5.05 g; 18.1 mmol). The mixture is stirred until complete solution is achieved. The resulting solution is added to 1-(tert-butylcarbamoyl)prop-1-en-2-yl 3-amino-6-chloro-5-[(cyclopropylmethyl)amino]pyrazine-2-carboxylate (example 5) (2.31 g; 6.05 mmol) in THF (50 ml). The mixture is stirred at r.t. for 3 d, then volatiles are evaporated. The residue is purified by RP-HPLC (modifier: trifluoro acetic acid (TFA) (C11H15ClN6OS).

Workup

  1. stirringThe mixture is stirred at r.t. for 3 d
  2. customvolatiles are evaporated
  3. customThe residue is purified by RP-HPLC (modifier

Sources & evidence

ORD record
ord-8fe48e495b0c457d898af570fc03823d
Source dataset
uspto-grants-2014_07
Patent number
US08791260B2

Reaction notes

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