Triethylamine → HCID 67022073, compound

HRID 1665575Notes

Reaction equation

HRID 1665575 reaction equation
[CH:1]12[N:9]([C:10]3[N:15]=[C:14]([N:16]4[CH:21]5[CH2:22][O:23][CH2:24][CH:17]4[CH2:18][O:19][CH2:20]5)[N:13]=[C:12]([C:25]4[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=4)[N:11]=3)[CH:5]([CH2:6][O:7][CH2:8]1)[CH2:4][O:3][CH2:2]2.CCN(CC)CC.ClC(Cl)(O[C:43](=[O:49])OC(Cl)(Cl)Cl)Cl.[CH3:51][N:52]1[CH2:57][CH2:56][N:55]([C:58]2[CH:64]=[CH:63][C:61]([NH2:62])=[CH:60][CH:59]=2)[CH2:54][CH2:53]1>C(Cl)Cl>[CH:5]12[N:9]([C:10]3[N:15]=[C:14]([N:16]4[CH:17]5[CH2:24][O:23][CH2:22][CH:21]4[CH2:20][O:19][CH2:18]5)[N:13]=[C:12]([C:25]4[CH:31]=[CH:30][C:28]([NH:29][C:43]([NH:62][C:61]5[CH:60]=[CH:59][C:58]([N:55]6[CH2:54][CH2:53][N:52]([CH3:51])[CH2:57][CH2:56]6)=[CH:64][CH:63]=5)=[O:49])=[CH:27][CH:26]=4)[N:11]=3)[CH:1]([CH2:8][O:7][CH2:6]1)[CH2:2][O:3][CH2:4]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 67021739HCID 67021739, compound

Product 1

HCID 67022073HCID 67022073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4,6-di(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-1,3,5-triazin-2-yl)aniline (120 mg, 0.281 mmol) in CH2Cl2 was added Et3N (0.237 mL, 1.69 mmol) and triphosgene (42 mg, 0.14 mmol). The mixture was stirred at room temperature for 15 minutes and 4-(4-methylpiperazin-1-yl)aniline (107 mg, 0.56 mmol) was added. The mixture was stirred at room temperature overnight. The solvent was removed, and the residue was subjected to HPLC separation to give the title compound (1TFA salt) MS (ESI) m/z 644.3306.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe solvent was removed
  3. customthe residue was subjected to HPLC separation

Sources & evidence

ORD record
ord-85e1b567021b4823a544740ba183c63d
Source dataset
uspto-grants-2011_10
Patent number
US08039469B2

Reaction notes

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