Hydrochloric Acid → HCID 178478823, compound

HRID 217932Notes

Reaction equation

HRID 217932 reaction equation
[ClH:1].C(OC([N:9]=[C:10]([NH:40]C(OC(C)(C)C)=O)[NH:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([NH:28][C:29]([C:31]2[C:36]([NH2:37])=[N:35][C:34]([NH2:38])=[C:33]([Cl:39])[N:32]=2)=[O:30])=[NH:27])=[CH:17][CH:16]=1)=O)(C)(C)C>CO>[ClH:39].[ClH:1].[NH2:37][C:36]1[C:31]([C:29]([NH:28][C:26]([NH:25][CH2:24][CH2:23][CH2:22][CH2:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][NH:11][C:10]([NH2:40])=[NH:9])=[CH:16][CH:17]=2)=[NH:27])=[O:30])=[N:32][C:33]([Cl:39])=[C:34]([NH2:38])[N:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454271HCID 178454271, compound

Product 1

HCID 178478823HCID 178478823, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12N HCl (15 mL) was added dropwise to an ice cooled solution of N-(4-{4-[2-(N′,N″-di-tert-butoxycarbonylguanidino)ethoxy]phenyl}butyl)-1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-guanidine 5 (370 mg, 0.56 mmole) in methanol (15 mL) over 1 min. After the addition, the cooling bath was removed, and the reaction was allowed to stir for 30 min. TLC (silica gel, methylene chloride/methanol/concentrated ammonium hydroxide, 3:3:1) indicated slow reaction progression. An additional 15 mL of 12N HCl was added dropwise at room temperature, and after 2 h, TLC indicated reaction completion. The solvent was evaporated and methanol (100 mL) was added and then evaporated below 30° C., this process was repeated a further three times and then the residue was placed under vacuum at 40° C. for 2 days to afford 300 mg (96%) of the pure product as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.57 (m, 4H), 2.56 (m, 2H), 3.52 (m, 2H), 4.02 (t, 2H), 4.60 (br s, 2H), 6.88 (d, 2H), 7.14 (d, 2H), 7.41 (m, 8H), 7.91 (t, 1H), 8.93 (m, 2H), 9.33 (t, 1H), 10.55 (s, 1H). mp 223-230. m/z (ESI)=463 [C19H27ClN10O2+H]+.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. additionAn additional 15 mL of 12N HCl was added dropwise at room temperature
  4. waitafter 2 h
  5. customreaction completion
  6. customThe solvent was evaporated
  7. additionmethanol (100 mL) was added
  8. customevaporated below 30° C.
  9. waitthe residue was placed under vacuum at 40° C. for 2 days

Sources & evidence

ORD record
ord-9e23caf2e39a4f1680f7ed9dc7ec1fd6
Source dataset
uspto-grants-2012_06
Patent number
US08198286B2

Reaction notes

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