1-Hydroxybenzotriazole → HCID 59170308, compound

HRID 1445939Notes

Reaction equation

HRID 1445939 reaction equation
NC(=O)C([C:5]1[C:9]2[C:10]([O:14][CH2:15]C(O)=O)=[N:11][CH:12]=[CH:13][C:8]=2[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]=1[CH3:26])=O.C(OC(=O)[C@H](CC(OCC1C=CC=CC=1)=O)N)C1C=CC=CC=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C=O.CN(C)C1C=CN=CC=1.ClCCl>[CH2:19]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH3:15])[C:9]=2[CH:5]=[C:6]1[CH3:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2808532Dibenzyl L-aspartateHCID 166569372-(3-(2-amino-2-oxoacetyl)-1-benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)acetic acid

Product 1

HCID 59170308HCID 59170308, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 2-(3-(2-amino-2-oxoacetyl)-1-benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)acetic acid ILY-II-1 (1.5 mmol) in dichloromethane/dimethylformamide (5:1) is added aspartic acid dibenzyl ester (313 mg 1.5 mmol), 4-dimethylaminopyridine (18 mg 0.15 mmol), 1-hydroxybenzotriazole (202 mg, 1.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (286 mg, 1.5 mmol), respectively and reaction mixture allows to stir at room temperature. After 6 hrs the reaction is diluted with dichloromethane and washed twice with 1N HCl and brine. The organic layer is dried with Na2SO4 and evaporated in vacuum. The residue is chromatographed on silica gel to give the titled compound 2.

Workup

  1. customrespectively and reaction mixture
  2. washwashed twice with 1N HCl and brine
  3. dry with materialThe organic layer is dried with Na2SO4
  4. customevaporated in vacuum
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-99732d84c1b14bfbaf23e9d01cbbf628
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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