Formic Acid → 1-[2-(tert-butyl)phenyl]-7-(3,5-dimethyl-4-isoxazolyl)-1H-imidazo[4,5-c]quinoline

HRID 1043009Notes

Reaction equation

HRID 1043009 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][CH2:19]C4C=CC=CC=4)=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:26])[O:4][N:3]=1.[CH:27]1[CH:28]=[CH:29][C:30]2N(O)N=N[C:31]=2[CH:32]=1.CCN=C=N[CH2:42][CH2:43][CH2:44]N(C)C.[CH3:48]CN(CC)CC.C(O)=O>C(Cl)Cl.O>[C:43]([C:31]1[CH:30]=[CH:29][CH:28]=[CH:27][C:32]=1[N:18]1[C:11]2[C:10]3[CH:9]=[CH:8][C:7]([C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:26])=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:17]=[CH:19]1)([CH3:44])([CH3:48])[CH3:42]

Participants

8

Reactant 5

HCID 284Formic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 672063207-(3,5-dimethyl-4-isoxazolyl)-N4-(phenylmethyl)-3,4-quinolinediamine2×

Product 1

HCID 529340411-[2-(tert-butyl)phenyl]-7-(3,5-dimethyl-4-isoxazolyl)-1H-imidazo[4,5-c]quinolineYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(3,5-dimethyl-4-isoxazolyl)-N4-(phenylmethyl)-3,4-quinolinediamine (for aq preparation see Intermediate 28, 0.2 g, 0.52 mmol) in DCM (10 ml) were added HOBT (0.081 g, 0.62 mmol), EDCI (0.118 g, 0.62 mmol), Et3N (0.062 g, 0.62 mmol) and formic acid (0.025 g, 0.52 mmol). The reaction mixture was stirred at room temperature overnight, then poured into water and extracted with DCM. The organic phase was washed with water, dried over Na2SO4 and concentrated. The crude solid was re-crystallized from EtOAc to give the title compound as off-white crystals (0.1 g, 48%). M.p: 216° C. 1H NMR (300 MHz, CDCl3, ppm) δ: 9.36 (s, 1H), 8.06 (s, 1H), 8.01 (s, 1H), 7.73 (d, J=7.2 Hz, 1H), 7.56 (dd, J=8.1, 8.1 Hz, 1H), 7.34 (dd, J=7.7, 7.7 Hz, 1H), 7.15-7.06 (m, 2H), 2.36 (s, 3H), 2.23 (s, 3H), 1.07 (s, 9H). LC-HRMS: ES+ exact mass calculated for C25H24N4O: 397.2028 MH+, found: 397.2021, Rt 3.03 min.

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude solid was re-crystallized from EtOAc

Sources & evidence

ORD record
ord-d2bf2ebdc99d4c0885f49984849a8735
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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