Acetamidine monohydrochloride → HCID 50991564, compound

HRID 1188089Notes

Reaction equation

HRID 1188089 reaction equation
[CH:1]1([N:4]([CH:25]2[CH2:27][CH2:26]2)[C:5]([C:7]2[N:22]([CH2:23][CH3:24])[C:10]3=[N:11][C:12]([N:19]=[C:20]=[S:21])=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.Cl.[C:29]([NH2:32])(=[NH:31])[CH3:30].CCN(C(C)C)C(C)C.N(C(OCC)=O)=NC(OCC)=O>CN(C=O)C>[CH:25]1([N:4]([CH:1]2[CH2:2][CH2:3]2)[C:5]([C:7]2[N:22]([CH2:23][CH3:24])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][N:32]=[C:29]([CH3:30])[N:31]=4)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 67170Acetamidine monohydrochlorideHCID 81531DiisopropylethylamineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58180531Imidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide, N,N-dicyclopropyl-6-ethyl-1,6-dihydro-4-isothiocyanato-1-methyl-

Product 1

HCID 50991564HCID 50991564, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N,N-dicyclopropyl-6-ethyl-4-isothiocyanato-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 121B, 0.042 g, 0.111 mmol), acetamidine hydrochloride (10.49 mg, 0.111 mmol), and Hünig's Base (0.058 mL, 0.333 mmol) in DMF (0.617 mL) was stirred at rt ON. Diethyl azodicarboxylate (0.088 mL, 0.222 mmol) was added and stirring continued at room temperature for 16 h. The reaction mixture was concentrated. The residue was taken up in MeOH and purified by preparative HPLC. N,N-Dicyclopropyl-6-ethyl-1-methyl-4-(3-methyl-1,2,4-thiadiazol-5-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (4.32 mg, 9% yield) was isolated as a pale yellow solid.

Workup

  1. stirringstirring
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f387861201754a3b98a73cd8b9d00132
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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