Triethylamine → HCID 67539410, compound

HRID 1192290Notes

Reaction equation

HRID 1192290 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:23][C:24]([O:27][C:28]([NH:30][C@@H:31]([C:40]([OH:42])=O)[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)=[O:29])([CH3:26])[CH3:25].Cl.Cl.[Br:45][C:46]1[CH:47]=[C:48]2[C:53](=[CH:54][CH:55]=1)[N:52]=[CH:51][N:50]=[C:49]2[N:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[C:24]([O:27][C:28](=[O:29])[NH:30][CH:31]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)[C:40]([N:59]1[CH2:60][CH2:61][N:56]([C:49]2[C:48]3[C:53](=[CH:54][CH:55]=[C:46]([Br:45])[CH:47]=3)[N:52]=[CH:51][N:50]=2)[CH2:57][CH2:58]1)=[O:42])([CH3:23])([CH3:25])[CH3:26]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 67538834HCID 67538834, compound

Product 1

HCID 67539410HCID 67539410, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDCI.HCl (230 mg, 1.2 mmol), HOBt (160 mg, 1.2 mmol) and Boc-D-4-chlorophenylalanine (240 mg, 1.2 mmol) were added to a stirred solution of 6-bromo-4-piperazin-1-yl-quinazoline bis-hydrochloride (360 mg, 0.98 mmol) and triethylamine (0.30 mL, 1.2 mmol) in DMF (8 mL) at room temperature under nitrogen. Stirred at room temperature overnight. Diluted with EtOAc (100 mL) and washed with water (3×50 mL.) Dried over Na2SO4 and concentrated in vacuo. The mixture was purified by silica gel column chromatography (100% EtOAc) to give [2-[4-(6-bromoquinazolin-4-yl)-piperazin-1-yl]-1-(4-chlorobenzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester as a yellow solid (320 mg, 57%.) MS (APCI+) [M+H]+ 575.9. 1H NMR (CDCl3, 400 MHz) δ 8.75 (1H, s), 7.95 (1H, s), 7.85-7.79 (2H, m), 7.30-7.27 (2H, m), 7.17 (2H, d, J7.1 Hz), 5.39 (1H, app. d, J8.2 Hz), 4.86 (1H, app. d, J 7.3 Hz), 3.83-3.60 (6H, m), 3.36-3.26 (2H, m), 3.04-2.96 (2H, m), 1.43 (9H, s).

Workup

  1. washwashed with water (3×50 mL.)
  2. dry with materialDried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe mixture was purified by silica gel column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-1d68b520f02b44d1860f596c58570519
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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