Hydrochloric Acid → HCID 178454187, compound

HRID 884730Notes

Reaction equation

HRID 884730 reaction equation
Cl.C1C2C(=CC=CC=2)C=C(C2C=CC(O)=CC=2)N=1.C1C=CC2N(O)N=NC=2C=1.[CH3:29][C:30]([O:33][C:34]([NH:36][C@H:37]([C:59]([OH:61])=[O:60])[CH2:38][CH2:39][CH2:40][N:41]=[C:42]([NH:51]C(OC(C)(C)C)=O)[NH:43]C(OC(C)(C)C)=O)=[O:35])([CH3:32])[CH3:31].CCN=C=NCCCN(C)C.Cl.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[C:34]([NH:36][C@H:37]([C:59]([OH:61])=[O:60])[CH2:38][CH2:39][CH2:40][NH:41][C:42](=[NH:43])[NH2:51])([O:33][C:30]([CH3:31])([CH3:29])[CH3:32])=[O:35]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11385959Boc-arg(boc)2-OHHCID 1354251244-(Isoquinolin-3-yl)phenol

Product 1

HCID 178454187HCID 178454187, compoundYield 182.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HCl (0.4 mL, 2 N) was added to 4-isoquinolin-3-yl-phenol (0.133 g, 0.6 mmol) in anhydrous DMF (5 mL). To this mixture were added HOBt (0.081 g, 0.6 mmol), Boc-Arg-(Boc)2-OH (0.285 g, 0.6 mmol), and EDCl (0.115 g, 0.6 mmol). N,N-Diisopropylethylamine (0.233 g, 1.8 mmol) was added and the mixture was stirred at rt for 24 h. Water (15 mL) was added and the white precipitate was filtered off, washed with water and dried under vacuum to give 0.3 g (74%) of the Boc-arginine derivative. The Boc derivative compound (0.3 g,) was dissolved in anhydrous dichloromethane (10 mL). HCl gas was bubbled into the solution at 0° C. for 4 h. A yellow precipitate was formed. The solvent was removed and the resulting sold was dried under vacuum. Triturating with ether gave 200 mg of 4-(isoquinolin-3-yl)phenyl 2-amino-5-guanidinopentanoate tetrahydrochloride (86%). MS (ES) m/z: 222.96 (M+1-Arg), 221.99 (M-Arg); Mp. 198-201° C.

Workup

  1. filtrationthe white precipitate was filtered off
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-acab87db82aa42ec82d1aa67eee5f342
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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