1-Hydroxybenzotriazole → HCID 178454187, compound

HRID 336632Notes

Reaction equation

HRID 336632 reaction equation
C1C2C(=CC=CC=2)C=C(C2C=CC(O)=CC=2)N=1.C1C=CC2N(O)N=NC=2C=1.[CH3:28][C:29]([O:32][C:33]([NH:35][C@H:36]([C:58]([OH:60])=[O:59])[CH2:37][CH2:38][CH2:39][N:40]=[C:41]([NH:50]C(OC(C)(C)C)=O)[NH:42]C(OC(C)(C)C)=O)=[O:34])([CH3:31])[CH3:30].CCN=C=NCCCN(C)C.Cl.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[C:33]([NH:35][C@H:36]([C:58]([OH:60])=[O:59])[CH2:37][CH2:38][CH2:39][NH:40][C:41](=[NH:42])[NH2:50])([O:32][C:29]([CH3:30])([CH3:28])[CH3:31])=[O:34]

Participants

8

Reactant 5

HCID 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

To a solution of 4-isoquinolin-3-yl-phenol (0.133 g, 0.6 mmol) in anhydrous DMF (5 mL) 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-Diisopropyl ethyl amine (0.233 g, 1.8 mmol) was added and the mixture was stirred at room temperature 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 above 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 solid was dried under vacuum. Triturating with ether gave 4-(isoquinolin-3-yl)phenyl 2-amino-5-guanidinopentanoate tetrahydrochloride (0.2 g, 86%). Selected data: 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-0b10b6c4ae0e4364bc16e63f2bedfa9f
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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