Triethylamine → (+/-)-{3-[[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester

HRID 1795980Notes

Reaction equation

HRID 1795980 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:41])[NH:14][CH2:15][CH2:16][CH2:17][NH:18][CH:19]([C:23]1[N:28]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](=[O:36])[C:26]2=[C:37]([Cl:40])[CH:38]=[CH:39][N:25]2[N:24]=1)[CH:20]1[CH2:22][CH2:21]1)([CH3:11])([CH3:10])[CH3:9].[CH3:42][C:43]1[CH:51]=[CH:50][C:46]([C:47](Cl)=[O:48])=[CH:45][CH:44]=1>C(Cl)Cl>[C:8]([O:12][C:13](=[O:41])[NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH:19]([C:23]1[N:28]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](=[O:36])[C:26]2=[C:37]([Cl:40])[CH:38]=[CH:39][N:25]2[N:24]=1)[CH:20]1[CH2:21][CH2:22]1)[C:47](=[O:48])[C:46]1[CH:50]=[CH:51][C:43]([CH3:42])=[CH:44][CH:45]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 69591847(3-{[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 69591850(+/-)-{3-[[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.425 mL, 3.05 mmol) was added to a 0° C. solution of (3-{[(3-benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-amino}-propyl)-carbamic acid tert-butyl ester (0.74 g, 1.52 mmol) and 4-methylbenzoyl chloride (0.403 mL, 3.05 mmol) in CH2Cl2 (10 mL) and was stirred at 0° for 1.5 h. The reaction mixture was quenched with 1 N HCl (30 mL) and extracted with CHCl3 (3×50 mL). The combined organic extracts were washed with saturated NaHCO3 (1×100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 3/1 hexane/EtOAc to afford the title compound (0.90 g, 98%) as a solid: MS (ESI+) 604 (M++H); HRMS (ESI+) calculated: 604.2691 (M++H). found: 604.2702 (M++H).

Workup

  1. customThe reaction mixture was quenched with 1 N HCl (30 mL)
  2. extractionextracted with CHCl3 (3×50 mL)
  3. washThe combined organic extracts were washed with saturated NaHCO3 (1×100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 3/1 hexane/EtOAc

Sources & evidence

ORD record
ord-e02dbf4da5c348c9954f469893d5fb38
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

Loading…