Guanidine Hydrochloride → N-(aminoiminomethyl)-5,6,7,8-tetrahydro-11-hydroxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxamide methanesulfonate

HRID 650088Notes

Reaction equation

HRID 650088 reaction equation
C([O:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]2[C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH2:19][N:10]3[C:11]=2[C:7]=1[CH:8]=[C:9]3[C:21]([O:23]CC)=O)(=O)C.Cl.[NH2:27][C:28]([NH2:30])=N.C[O-].[Na+].[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[NH:39]1C2C(=CC=CC=2)C=C1C(N)=O>CN(C)C=O>[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[NH2:39][N:27]=[CH:28][NH:30][C:21]([C:9]1[N:10]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15](=[O:20])[C:12]3[CH:13]=[CH:14][C:6]([CH2:5][OH:4])=[C:7]([CH:8]=1)[C:11]2=3)=[O:23]

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 70235751ethyl 5,6,7,8-tetrahydro-11-acetoxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylateHCID 86754736Indole-2-carboxamide methanesulfonate

Product 1

HCID 136340739N-(aminoiminomethyl)-5,6,7,8-tetrahydro-11-hydroxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxamide methanesulfonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In accordance with the process described in Example 1 except for using ethyl 5,6,7,8-tetrahydro-11-acetoxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylate (2.13 g, 6.20 mmol), guanidine hydrochloride (5.92 g, 62 mmol), sodium methoxide (3.35 g, 62 mmol) and N,N-dimethylformamide (50 ml), 1.07 g of N-(aminoiminomethyl)-5,6,7, 8-tetrahydro-11-hydroxymethyl-8-oxo-4H-azcino[3.2.1-hi]indole-2-carboxamide methanesulfonate was obtained.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-8a1302d365f54bd8809617609eb0a465
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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