Triethylamine → HCID 178512394, compound

HRID 77507

Reaction equation

HRID 77507 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](SC)=[NH:14])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.Cl.Cl.[NH2:19][CH:20]1[CH:25]2[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]2)[CH2:21]1.C(N(CC)CC)C>O1CCCC1>[N:22]12[CH2:27][CH2:26][CH:25]([CH2:24][CH2:23]1)[CH:20]([NH:19][C:13]([NH:12][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=1)=[O:11])=[NH:14])[CH2:21]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 1404443183,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide2×

Product 1

HCID 178512394HCID 178512394, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

3,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide (Intermediate 3, 250 mg, 0.88 mmol) is dissolved in tetrahydrofuran (20 mL) and to the solution 3-amino-quinuclidine dihydrochloride (211 mg, 1.06 mmol) and triethylamine (0.61 mL, 4.41 mmol) are added. The mixture is heated at 80° C. for 24 hours. The solid is removed by filtration and the is filtrate evaporated and purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient) obtaining the title compound (45 mg).

Workup

  1. additionare added
  2. customThe solid is removed by filtration
  3. customthe is filtrate evaporated
  4. custompurified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient)

Sources & evidence

ORD record
ord-51243bcc145f4f6d952cda21f136ef1f
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Linked notes

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