Triphosgene → HCID 52943744, compound

HRID 1513422Notes

Reaction equation

HRID 1513422 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([N:13]3[CH:18]4[CH2:19][CH2:20][CH:14]3[CH2:15][O:16][CH2:17]4)[N:10]=[C:9]([C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.ClC(Cl)(O[C:32](=[O:38])OC(Cl)(Cl)Cl)Cl.[CH3:40][N:41]1[CH2:46][CH2:45][N:44]([C:47]2[CH:53]=[CH:52][C:50]([NH2:51])=[CH:49][CH:48]=2)[CH2:43][CH2:42]1>>[CH3:40][N:41]1[CH2:42][CH2:43][N:44]([C:47]2[CH:53]=[CH:52][C:50]([NH:51][C:32]([NH:25][C:24]3[CH:26]=[CH:27][C:21]([C:9]4[N:8]=[C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[N:12]=[C:11]([N:13]5[CH:14]6[CH2:20][CH2:19][CH:18]5[CH2:17][O:16][CH2:15]6)[N:10]=4)=[CH:22][CH:23]=3)=[O:38])=[CH:49][CH:48]=2)[CH2:45][CH2:46]1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 670216444-[4-Morpholin-4-yl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-1,3,5-triazin-2-yl]aniline

Product 1

HCID 52943744HCID 52943744, compoundYield 9.1%

Procedure

Following the procedure described in example 34, reaction of 4-[4-morpholin-4-yl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-1,3,5-triazin-2-yl]aniline (22 mg, 0.06 mmol) (22 mg, 0.06 mmol, triphosgene (18 mg, 0.06 mmol) and 4-(4-methylpiperazin-1-yl)aniline (54 mg, 0.18 mmol) gave the title compound as off-white solid (2TFA salt, 3.2 mg, 7% yield). MS (ESI) m/z 586.6.

Sources & evidence

ORD record
ord-90e7b40f896644b592745c0c956ca6fc
Source dataset
uspto-grants-2012_07
Patent number
US08217036B2

Reaction notes

Loading…