Triethylamine → HCID 15547425, compound

HRID 1385104Notes

Reaction equation

HRID 1385104 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]([NH:29][C:30]4[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=4)=[O:28])[CH:25]=3)[C:20]([CH2:39][CH3:40])=[N:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.Cl.[CH2:42]([O:49][NH2:50])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:42]([O:49][NH:50][C:34]([C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:27]([C:24]2[CH:25]=[C:26]3[C:21]([C:20]([CH2:39][CH3:40])=[N:19][N:18]3[CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:22][CH:23]=2)=[O:28])=[CH:38][CH:37]=1)=[O:35])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21183693HCID 21183693, compound

Product 1

HCID 15547425HCID 15547425, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

140 mg (0.728 mmol, 1.1 equiv) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added in one portion to a room temperature solution of 250 mg (0.662 mmol, 1.0 equiv) 4-[(1-cyclopentyl-3-ethyl-1H-indazole-6-carbonyl)-amino]-benzoic acid, 106 mg (0.662 mmol, 1.0 equiv) O-benzylhydroxylamine hydrochloride, 101 mg (0.662 mmol, 1.0 equiv) 1-hydroxybenzotriazole hydrate, and 194 μL (1.39 mmol, 2.1 equiv) triethylamine in 25 mL CH2Cl2. After 18 hours, 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 (2% CH3OH/CH2Cl2, flash) to give 212 mg (66%) of white crystalline solid: mp 194-198° C.; Anal. calcd for C28H30N4O3: C, 72.17; H, 7.10; N, 11.61. Found: C, 71.62; H, 6.47; N, 11.85.

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 (2% CH3OH/CH2Cl2, flash)

Sources & evidence

ORD record
ord-b289a90cbf954c439cd8fb62776c1c90
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

Loading…