1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86681609, compound

HRID 571186Notes

Reaction equation

HRID 571186 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[Cl:13][C:14]1[CH:15]=[N+:16]([O-:39])[CH:17]=[C:18]([Cl:38])[C:19]=1[CH2:20][C@@H:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]([F:32])[F:31])=[C:25]([O:33][CH2:34][CH:35]2[CH2:37][CH2:36]2)[CH:24]=1)[OH:22].[O:40]=[C:41]1[C:50](=[O:51])[NH:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:42]1[CH2:52][C:53](O)=[O:54]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[N+:16]([O-:39])[CH:17]=[C:18]([Cl:38])[C:19]=1[CH2:20][C@@H:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]([F:32])[F:31])=[C:25]([O:33][CH2:34][CH:35]2[CH2:37][CH2:36]2)[CH:24]=1)[O:22][C:53](=[O:54])[CH2:52][N:42]1[C:43]2[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=2)[NH:49][C:50](=[O:51])[C:41]1=[O:40]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 129386642-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acidHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 86681609HCID 86681609, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1-Ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDC HCl) (59 mg, 0.309 mmol) was added to a solution of compounds (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (100 mg, 0.238 mmol), 2-(2,3-dioxo-3,4-dihydroquinoxalin-1(2H)-yl)acetic acid (63 mg, 0.286 mmol) and 4-dimethylaminopyridine (6 mg, 0.048 mmol) in CH2Cl2 (1 mL) at room temperature under nitrogen atmosphere. The mixture was stirred at room temperature overnight. The mixture was then diluted with CH2Cl2 (5 mL) and washed with NaHCO3 saturated solution (5 mL), HCL 0.1 N (5 mL) and brine (5 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated, to yield 70 mg of the title compound (80% yield). MS/ESI+ 621.09 [MH]+

Workup

  1. washwashed with NaHCO3 saturated solution (5 mL), HCL 0.1 N (5 mL) and brine (5 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ca147a463cbc492684bd9837e6759d9f
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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