4-Methylmorpholine → N-(3-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methyl-phenyl)-3-(morpholin-4-yl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055666Notes

Reaction equation

HRID 1055666 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:37]=[CH:36][C:13]([CH2:14][N:15]2[CH:19]=[C:18]([C:20]3[CH:21]=[C:22]4[N:27]([C:28]5[CH:29]=[C:30]([CH:32]=[CH:33][C:34]=5[CH3:35])[NH2:31])[CH:26]=[CH:25][N:23]4[N:24]=3)[CH:17]=[N:16]2)=[CH:12][CH:11]=1.[N:38]1([C:44]2[CH:45]=[C:46]([CH:50]=[C:51]([S:53]([F:58])([F:57])([F:56])([F:55])[F:54])[CH:52]=2)[C:47](O)=[O:48])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[OH-].[Na+]>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[CH:19]=[C:18]([C:20]3[CH:21]=[C:22]4[N:27]([C:28]5[CH:29]=[C:30]([NH:31][C:47](=[O:48])[C:46]6[CH:50]=[C:51]([S:53]([F:58])([F:54])([F:55])([F:56])[F:57])[CH:52]=[C:44]([N:38]7[CH2:43][CH2:42][O:41][CH2:40][CH2:39]7)[CH:45]=6)[CH:32]=[CH:33][C:34]=5[CH3:35])[CH:26]=[CH:25][N:23]4[N:24]=3)[CH:17]=[N:16]2)=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896996563-(Morpholin-4-yl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 897000263-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylaniline trifluoroacetate

Product 1

HCID 89699732N-(3-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methyl-phenyl)-3-(morpholin-4-yl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

82 mg (0.16 mmol) of the compound of Example 8A, 59 mg (0.18 mmol) of the compound of Example 18A and 73 mg (0.192 mmol) of HATU were dissolved in 1 ml of DMF. 53 μl (0.48 mmol) of 4-methylmorpholine were then added. After the reaction mixture had been stirred at RT for 16 h, 10 ml of 0.1 M aqueous sodium hydroxide solution were added, whereupon the product precipitated as a solid. The mixture was stirred for another 10 min, and the product was then filtered off with suction, washed with water and dried under high vacuum. This gave 104 mg (70% of theory, 77% pure) of the title compound as a greyish-brown solid.

Workup

  1. customprecipitated as a solid
  2. stirringThe mixture was stirred for another 10 min
  3. filtrationthe product was then filtered off with suction
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-631c8c1ae1aa4d999e76d852a4f27d5e
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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