Triethylamine → HCID 69214597, compound

HRID 747862Notes

Reaction equation

HRID 747862 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:17]2[CH:18]=[C:19]([C:22](O)=[O:23])[CH:20]=[CH:21][C:16]2=[CH:15][N:14]=1.C(N=C=NCCCN(C)C)C.O[N:37]1[C:41]2[CH:42]=[CH:43][CH:44]=CC=2N=N1.C(N(CC)CC)C.C1(NC)CC1>CN(C=O)C>[CH:42]1([CH2:41][NH:37][C:22]([C:19]2[CH:20]=[CH:21][C:16]3[N:17]([C:13]([C:3]4[C:4]([C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=5)=[N:5][O:6][C:2]=4[CH3:1])=[N:14][CH:15]=3)[CH:18]=2)=[O:23])[CH2:44][CH2:43]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11029756N-MethylcyclopropanamineHCID 58946092HCID 58946092, compound

Product 1

HCID 69214597HCID 69214597, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution containing 3-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,5-a]pyridine-6-carboxylic acid (58 mg, 0.18 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (52 mg, 0.27 mmol), 1-hydroxybenzotriazole (24 mg, 0.18 mmol), triethylamine (60 μL, 0.45 mmol) and cyclopropyl methylamine (20 mg, 0.27 mmol) in DMF (1 mL) was stirred at room temperature overnight. Purification by preparative HPLC on reversed phase (0.1% aqueous ammonia (25%) afforded the title compound (34 mg, 50%) as a light yellow solid. MS: m/e: 373.3 [M+H]+.

Workup

  1. customPurification by preparative HPLC on reversed phase (0.1% aqueous ammonia (25%)

Sources & evidence

ORD record
ord-021f80b6142e45a3acebad25e9bc0119
Source dataset
uspto-grants-2008_07
Patent number
US07399769B2

Reaction notes

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