Hydrochloric Acid → (S)-1,1-Bis-[3-(3-carboxymethoxy-phenyl)-propyl]-3-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-piperidinium chloride

HRID 509909Notes

Reaction equation

HRID 509909 reaction equation
FC(F)(F)C([O-])=O.[NH2:8][C:9]1[C:10]([C:17]([NH:19][C@H:20]2[CH2:25][CH2:24][CH2:23][N+:22]([CH2:41][CH2:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([O:50][CH2:51][C:52]([O:54]C)=[O:53])[CH:45]=3)([CH2:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][C:37]([O:39]C)=[O:38])[CH:30]=3)[CH2:21]2)=[O:18])=[N:11][C:12]([Cl:16])=[C:13]([NH2:15])[N:14]=1.Cl>O1CCOCC1>[Cl-:16].[C:52]([CH2:51][O:50][C:46]1[CH:45]=[C:44]([CH2:43][CH2:42][CH2:41][N+:22]2([CH2:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][C:37]([OH:39])=[O:38])[CH:30]=3)[CH2:23][CH2:24][CH2:25][C@H:20]([NH:19][C:17]([C:10]3[C:9]([NH2:8])=[N:14][C:13]([NH2:15])=[C:12]([Cl:16])[N:11]=3)=[O:18])[CH2:21]2)[CH:49]=[CH:48][CH:47]=1)([OH:54])=[O:53]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117856343(S)3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium trifluoroacetate

Product 1

HCID 117856257(S)-1,1-Bis-[3-(3-carboxymethoxy-phenyl)-propyl]-3-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-piperidinium chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium trifluoroacetate (2.67 g, 3.8 mmol)) is dissolved in dioxane (20 ml) and 6N HCl (20 ml, 120 mmol) and stirred at room temperature for 3 days and solvent is removed in vacuo. LC (method L)): tR=1.06 min; Mass spectrum (ESI+): m/z=655 [M]+.

Workup

  1. customsolvent is removed in vacuo

Sources & evidence

ORD record
ord-000057c990134e39b44dccb863faf61b
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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