Triethylamine → HCID 69591863, compound

HRID 1795950Notes

Reaction equation

HRID 1795950 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]([C:15]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:28])[C:18]2=[CH:29][CH:30]=[C:31]([Cl:32])[N:17]2[N:16]=1)[CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[C:41]1([CH3:50])[CH:46]=[CH:45][C:44]([C:47](Cl)=[O:48])=[CH:43][CH:42]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:12]([C:15]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:28])[C:18]2=[CH:29][CH:30]=[C:31]([Cl:32])[N:17]2[N:16]=1)[CH2:13][CH3:14])[C:47](=[O:48])[C:44]1[CH:45]=[CH:46][C:41]([CH3:50])=[CH:42][CH:43]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 69591864HCID 69591864, compound

Product 1

HCID 69591863HCID 69591863, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (±)-N-{3-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-propyl}-carbamic acid tert-butyl ester (0.51 g, 1.08 mmol) and Et3N (0.25 mL, 1.79 mmol) in CH2Cl2 (10 mL) at rt was added p-toluoyl chloride (0.21 mL, 1.58 mmol) under N2 and stirred at rt for 3 hr. The reaction mixture was diluted with CH2Cl2 to 100 mL, washed with aq. NaHCO3 solution (30 mL), dried over MgSO4. Concentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1.5:8.5 to 1:3) gave the title compound as pale oil (0.43 g, 67%): 1H NMR (CDCl3) δ 7.30 (m, 2H), 7.24 (m, 1H), 7.15 (m, 2H), 7.10 (d, 1H, J=4.4 Hz), 6.53 (d, 1H, J=4.4 Hz), 5.91 (m, 1H), 4.95 (m, 1H), 3.35 (m, 2H), 2.70 (m, 1H), 2.36 (s, 3H), 2.05 (m, 1H), 1.95 (m, 1H), 1.43 (m, 3H), 1.35 (s, 9H), 0.67 (m, 3H); MS (ESI+) 592.15 (M++H).

Workup

  1. washwashed with aq. NaHCO3 solution (30 mL)
  2. dry with materialdried over MgSO4
  3. concentrationConcentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1.5:8.5 to 1:3)

Sources & evidence

ORD record
ord-44f8a2ba46e84e6e9938302d02504cce
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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