1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58762839, compound

HRID 858070Notes

Reaction equation

HRID 858070 reaction equation
C(NC1SC(S(NC2C=CC(CC([NH:24][C:25]3[C:26](=[O:45])[N:27]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[F:44])[C:28](=[O:36])[N:29](CC4CC4)[C:30]=3[NH2:31])=O)=CC=2)(=O)=O)=C(C)N=1)(=O)C.Cl.CN(C)CCCN=C=NCC.[Cl:58][C:59]1[N:63]([CH3:64])[N:62]=[C:61]([CH3:65])[C:60]=1[S:66]([NH:69][C:70]1[CH:71]=[CH:72][C:73]([CH2:76][C:77]([OH:79])=O)=[N:74][CH:75]=1)(=[O:68])=[O:67].NC1C(=O)N(CC2C=CC=CC=2F)C(=O)NC=1N>CO.C(Cl)(Cl)Cl>[NH2:31][C:30]1[NH:29][C:28](=[O:36])[N:27]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[F:44])[C:26](=[O:45])[C:25]=1[NH:24][C:77](=[O:79])[CH2:76][C:73]1[CH:72]=[CH:71][C:70]([NH:69][S:66]([C:60]2[C:61]([CH3:65])=[N:62][N:63]([CH3:64])[C:59]=2[Cl:58])(=[O:67])=[O:68])=[CH:75][N:74]=1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 587628315,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dioneHCID 58762844[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetic acidHCID 587628482-[4-(2-acetylamino-4-methyl-thiazole-5-sulfonylamino)-phenyl]-N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide

Product 1

HCID 58762839HCID 58762839, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Prepared as for 2-[4-(2-acetylamino-4-methyl-thiazole-5-sulfonylamino)-phenyl]-N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide (example 10, step 1) except that the coupling was performed using 1 [3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride as the coupling reagent and [5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetic acid and 5,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione were used as the coupling partners. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 10/90 methanol/chloroform) afforded N-[6-amino-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetamide (42%) as an off white solid; LRMS for C29H29ClFN7O4S (M+H)+ at m/z=577/579.

Sources & evidence

ORD record
ord-edd11bc1936b45b59f8946ba67062f41
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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