Hydrochloric Acid → HCID 131725696, compound

HRID 1795951Notes

Reaction equation

HRID 1795951 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:24]1[N:29]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](=[O:37])[C:27]2=[CH:38][CH:39]=[C:40]([Cl:41])[N:26]2[N:25]=1)[CH2:22][CH3:23])[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(C)(C)C.Cl>O1CCOCC1>[ClH:41].[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:24]1[N:29]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](=[O:37])[C:27]2=[CH:38][CH:39]=[C:40]([Cl:41])[N:26]2[N:25]=1)[CH2:22][CH3:23])[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69591863HCID 69591863, compound

Product 1

HCID 131725696HCID 131725696, compoundYield 182.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of {3-[[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester (0.42 g, 0.71 mmol) and 4 N HCl in dioxane (4.5 mL, 18 mmol) in dioxane (5 mL) stirred at rt for 6.5 h. After concentration the mixture was diluted with water, washed with Et2O (50 mL) and lyophilized to obtain the title compound (0.342 g, 91%): 13C NMR (DMSO-d6) δ 153.0, 128.6, 128.3, 126.9, 125.8, 125.5, 117.6, 115.3, 110.0, 108.3, 53.8, 44.2, 41.2, 36.2, 28.3, 23.4, 20.6, 10.1; MS (ESI+) 492.16, 493.22 (M++H).

Workup

  1. concentrationAfter concentration the mixture
  2. additionwas diluted with water
  3. washwashed with Et2O (50 mL)

Sources & evidence

ORD record
ord-347ac4639f44463491750c544b8c2458
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

Loading…