1-Methyl-1,2,3,4-tetrahydroquinolin-7-amine → 6-(2-chlorophenyl)-2-[(1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)amino]imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

HRID 2370616Notes

Reaction equation

HRID 2370616 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[CH3:25][N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([NH2:36])[CH:34]=2)[CH2:29][CH2:28][CH2:27]1>CS(C)=O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[CH:15]=[N:14][C:13]([NH:36][C:33]3[CH:34]=[C:35]4[C:30]([CH2:29][CH2:28][CH2:27][N:26]4[CH3:25])=[CH:31][CH:32]=3)=[N:12][C:11]=2[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12

Participants

4

Reactant 2

HCID 112174211-Methyl-1,2,3,4-tetrahydroquinolin-7-amineHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 601686846-(2-chlorophenyl)-2-[(1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)amino]imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

A mixture of Example 1E (60.0 mg, 0.167 mmol) and 1-methyl-1,2,3,4-tetrahydroquinolin-7-amine (48.7 mg, 0.300 mmol) was heated in a capped vial at 90° C. for 1 hour. After cooling, the residue was treated with dimethylsulfoxide/methanol (2 mL). The precipitate was filtered, washed with methanol and water, and oven-dried to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.77-1.99 (m, 2H), 2.69 (t, J=6.26 Hz, 2H), 2.90 (s, 3H), 3.11-3.28 (m, 2H), 6.92 (d, J=7.93 Hz, 1H), 7.02 (d, J=7.32 Hz, 1H), 7.07 (s, 1H), 7.18 (s, 1H), 7.50-7.65 (m, 3H), 7.69-7.74 (m, 2H), 9.09 (s, 1H), 10.53 (s, 1H). MS (ESI+) m/z 458.2 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with methanol and water
  4. customoven-dried

Sources & evidence

ORD record
ord-1fb9f48dbf264099a7447ad3013ffef8
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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