Hydrochloric Acid → HCID 178512152, compound

HRID 217931Notes

Reaction equation

HRID 217931 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH2:35])=[N:23][C:24]([C:26]2[C:31]([NH2:32])=[N:30][C:29]([NH2:33])=[C:28]([Cl:34])[N:27]=2)=[O:25])=[CH:13][CH:12]=1)(C)(C)C.Cl.C(Cl)Cl.CO>CO>[NH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:23][C:24]([C:26]2[C:31]([NH2:32])=[N:30][C:29]([NH2:33])=[C:28]([Cl:34])[N:27]=2)=[O:25])=[NH:35])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 178453722[2-(4-{4-[N'-(3,5-Diamino-6-chloropyrazine-2-carbonyl)guanidino]butyl}phenoxy)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 178512152HCID 178512152, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[2-(4-{4-[N-(3,5-Diamino-6-chloropyrazine-2-carbonyl)guanidino]butyl}phenoxy)ethyl]-carbamic acid tert-butyl ester 3 (2.63 g, 5.0 mmol) was dissolved in methanol (25 mL). 12N HCl (30 mL) was added in 10 ml portions. After stirring for 1 h, the reaction was complete by TLC (silica gel, methylene chloride/methanol/concentrated ammonium hydroxide, 100:10:1). The solvent was evaporated and methanol (300 mL) was added and, this process was repeated. The residue was placed under high vacuum overnight to afford the product (2.65 g, 99%) as a yellow solid, which was used without further manipulation. 1H NMR (300 MHz, DMSO-d6) δ 1.58 (m, 4H), 2.57 (m, 2H), 3.16 (m, 2H), 3.37 (m, 2H), 4.18 (t, 2H), 6.91 (d, 2H), 7.15 (d, 2H), 7.45 (m, 4H), 8.45 (br s, 3H), 9.03 (br s, 2H), 9.46 (t, 1H), 10.63 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionmethanol (300 mL) was added
  3. customwas placed under high vacuum overnight

Sources & evidence

ORD record
ord-edb1482c5df04022a9a347b647de6e16
Source dataset
uspto-grants-2012_06
Patent number
US08198286B2

Reaction notes

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