1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Edoxaban

HRID 1986040Notes

Reaction equation

HRID 1986040 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C@@H:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:5][CH2:4][C@@H:3]1[NH:13][C:14](=[O:25])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)=[O:16].O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:38][N:39]1[CH2:44][CH2:43][C:42]2[N:45]=[C:46]([C:48](O)=[O:49])[S:47][C:41]=2[CH2:40]1.Cl.CN(C)CCCN=C=NCC>CC(N(C)C)=O.O.C(N(CC)CC)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[C:14]([NH:13][C@H:3]2[CH2:4][CH2:5][C@H:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:7][C@H:2]2[NH:1][C:48]([C:46]2[S:47][C:41]3[CH2:40][N:39]([CH3:38])[CH2:44][CH2:43][C:42]=3[N:45]=2)=[O:49])=[O:25])=[N:19][CH:20]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 111490315-Methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid--hydrogen chloride (1/1)HCID 59676986EthanediaMide iMpurity F

Product 1

HCID 10280735EdoxabanYield 81.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 31374DimethylacetamideSolvent

Procedure

N1-{(1S,2R,4S)-2-Amino-4-[(dimethylamino)carbonyl]cyclohexyl}-N2-(5-chloropyridin-2-yl)ethanediamide (553.4 mg) was dissolved in dimethylacetamide (7 mL), and to the solution were added 1-hydroxybenzotriazole monohydrate (245.1 mg), 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride (386.0 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (345.0 mg) at room temperature. The resultant mixture was stirred for 13 hours, and triethylamine and water were added thereto. The precipitated crystals were collected by filtration, and were dried, to thereby give 674.1 mg of the title compound.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. customwere dried

Sources & evidence

ORD record
ord-915072779a4c4453842ae556f81ef9eb
Source dataset
uspto-grants-2009_06
Patent number
US07547786B2

Reaction notes

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