Triethylamine → HCID 54529817, compound

HRID 1385111Notes

Reaction equation

HRID 1385111 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH:13]1([N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]([OH:29])=O)[CH:25]=3)[C:20]([CH2:30][CH3:31])=[N:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.Cl.[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH2:37].O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH:37][C:27]([C:24]1[CH:25]=[C:26]2[C:21]([C:20]([CH2:30][CH3:31])=[N:19][N:18]2[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)=[CH:22][CH:23]=1)=[O:29]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15545851HCID 15545851, compound

Product 1

HCID 54529817HCID 54529817, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

134 mg (0.697 mmol, 1.0 equiv) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added in one portion to a room temperature solution of 180 mg (0.697 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxylic acid, 87.5 mg (0.697 mmol, 1.0 equiv) glycine methyl ester hydrochloride, 107 mg (0.697 mmol, 1.0 equiv) 1-hydroxybenzotriazole hydrate, and 194 μL (1.39 mmol, 2.0 equiv) triethylamine in 5 mL CH2Cl2. After 18 h, the reaction mixture was diluted with 150 mL ethyl acetate, washed 1×25 mL each 1N HCl, H2O, brine, and dried over Na2SO4. The crude product was purified on a silica gel column (40% ethyl acetate/hexanes, flash) to give 187 mg (66%) of a white waxy solid: mp 89-93° C.; Anal. calcd for C18H23N3O3; C, 65.63; H, 7.04; N, 12.76. Found: C, 65.74; H, 7.02; N, 12.74.

Workup

  1. washwashed 1×25 mL each 1N HCl, H2O, brine
  2. dry with materialdried over Na2SO4
  3. customThe crude product was purified on a silica gel column (40% ethyl acetate/hexanes, flash)
  4. customto give 187 mg (66%) of a white waxy solid

Sources & evidence

ORD record
ord-fdd8b5b44c894d2ab39d222814a6db80
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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