3-Chloro-4-morpholinoaniline → HCID 58711988, compound

HRID 2374892Notes

Reaction equation

HRID 2374892 reaction equation
BrC1C=C(C=CC=1)C(NC(C1N=NC(NC2C=C(S(CC)(=O)=O)C=CC=2OC)=NC=1)C)=O.[Br:33][C:34]1[CH:35]=[C:36]([CH:52]=[CH:53][CH:54]=1)[C:37]([NH:39][CH:40]([C:42]1[N:47]=[N:46][C:45](S(C)(=O)=O)=[N:44][CH:43]=1)[CH3:41])=[O:38].[Cl:55][C:56]1[CH:57]=[C:58]([CH:60]=[CH:61][C:62]=1[N:63]1[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1)[NH2:59].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[Br:33][C:34]1[CH:35]=[C:36]([CH:52]=[CH:53][CH:54]=1)[C:37]([NH:39][CH:40]([C:42]1[N:47]=[N:46][C:45]([NH:59][C:58]2[CH:60]=[CH:61][C:62]([N:63]3[CH2:64][CH2:65][O:66][CH2:67][CH2:68]3)=[C:56]([Cl:55])[CH:57]=2)=[N:44][CH:43]=1)[CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 1086613-Chloro-4-morpholinoanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 58711953HCID 58711953, compound2×HCID 587120043-bromo-N-[1-(3-{[5-(ethylsulfonyl)-2-methoxyphenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide

Product 1

HCID 58711988HCID 58711988, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner as described for Intermediate 23, 3-bromo-N{1-[3-(methylsulfonyl)-1,2,4-triazin-6-yl]ethyl}benzamide (Intermediate 6) (200 mg, 0.52 mmol), 3-chloro-4-morpholin-4-ylaniline (200 mg, 0.94 mmol) and 4-toluenesulfonic acid monohydrate (20 mg) in tetrahydrofuran (10 mL) gave 3-bromo-N-(1-{3-[(3-chloro-4-morpholin-4-ylphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (0.045 g) as a white solid. MS m/z 517, 519 (M+1, M+3).

Sources & evidence

ORD record
ord-19542395312246b0a01168df2b3d4bf6
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

Loading…