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

HRID 1795981Notes

Reaction equation

HRID 1795981 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]([C:16]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:29])[C:19]2=[C:30]([Cl:33])[CH:31]=[CH:32][N:18]2[N:17]=1)[CH:13]1[CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:42][C:43]1[CH:51]=[CH:50][C:46]([C:47](Cl)=[O:48])=[CH:45][CH:44]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:12]([C:16]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:29])[C:19]2=[C:30]([Cl:33])[CH:31]=[CH:32][N:18]2[N:17]=1)[CH:13]1[CH2:14][CH2:15]1)[C:47](=[O:48])[C:46]1[CH:50]=[CH:51][C:43]([Cl:42])=[CH:44][CH:45]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl 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 69591786{3-[[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl) cyclopropyl-methyl]-(4-chloro-benzoyl)-amino]-propyl}-carbamic acid tert-butyl esterYield 38.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(±)-(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 (Example 22H, 16 mg, 0.033 mmol) in methylene chloride (1.5 mL) was treated with triethylamine (5 μL, 0.036 mmol), and p-chlorobenzoyl chloride (6 mg, 0.034 mmol) at 0° C. and the resulting mixture was stirred at room temperature for 1 h. The mixture was diluted with methylene chloride (5 mL), washed with saturated sodium bicarbonate, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes to give the title compound (8 mg) as a clear oil: MS (ESI+) 604.2 (M++H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0587bf5382f74ec9b474c1c7dcc3d958
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

Loading…