Triethylamine → HCID 69591802, compound

HRID 1795959Notes

Reaction equation

HRID 1795959 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=[CH:30][CH:31]=[C:32]([Cl:33])[N:18]2[N:17]=1)[CH:13]1[CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[C:42]1([CH3:51])[CH:47]=[CH:46][C:45]([C:48](Cl)=[O:49])=[CH:44][CH:43]=1>C(Cl)Cl.CCOC(C)=O>[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:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:20](=[O:29])[C:19]2=[CH:30][CH:31]=[C:32]([Cl:33])[N:18]2[N:17]=1)[CH:13]1[CH2:14][CH2:15]1)[C:48](=[O:49])[C:45]1[CH:46]=[CH:47][C:42]([CH3:51])=[CH:43][CH:44]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 69591866HCID 69591866, compound

Product 1

HCID 69591802HCID 69591802, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (±)-(3-{[(3-benzyl-7-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 (0.30 g, 0.62 mmol) and Et3N (0.13 mL, 0.93 mmol) in CH2Cl2 (10 mL) at rt was added p-toluoyl chloride (0.10 mL, 0.76 mmol) under N2 and it was stirred at rt for 50 min. The reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 solution, and dried over MgSO4. Concentration and purification of the residue by flash column chromatography (SiO2, EtOAc/hexane 1:4) gave the title compound as an oil (0.244 g, 66%): 1H NMR (CDCl3) δ 7.22 (m, 2H), 7.13 (m, 3H), 7.04 (d, 1H, J=4.4 Hz), 6.48 (d, 1H, J=4.4 Hz), 5.90 (d, 1H, J=15.95 Hz), 5.12 (d, 1H, J=9.9 Hz), 4.83 (d, 1H, J=15.95 Hz), 4.03 (m, 1H), 3.54 (m, 1H), 3.45 (m, 1H), 2.74 (m, 2H), 2.31 (s, 3H), 1.66 (m, 2H), 1.29 (s, 9H), 1.19 (m, 3H), 0.80 (m, 1H), 0.42 (m, 1H), 0.32 (m, 2H); 3C NMR (CDCl3) δ 172.9, 155.7, 154.6, 148.8, 139.8, 136.8, 133.2, 129.2, 128.8, 127.7, 126.8, 126.3, 117.7, 117.2, 110.3, 108.5, 57.9, 44.4, 42.7, 37.9, 30.9, 28.2, 21.4, 13.4, 5.24, 3.80; MS (ESI+) 626.16, 628.14 (M++Na).

Workup

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationConcentration and purification of the residue by flash column chromatography (SiO2, EtOAc/hexane 1:4)

Sources & evidence

ORD record
ord-2ea2070fb5ad408897c49f66ae715970
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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