Ammonia → (S)-N-Methyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzenesulfonamide

HRID 1052774Notes

Reaction equation

HRID 1052774 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:20]3[C:19]([NH:21][C@H:22]([C:24]4[N:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:28](=[O:36])[C:27]5=[C:37]([CH3:40])[CH:38]=[CH:39][N:26]5[N:25]=4)[CH3:23])=[N:18][CH:17]=[N:16][C:15]=3[N:14](COCC[Si](C)(C)C)[CH:13]=2)[CH:7]=1)(=[O:5])=[O:4].FC(F)(F)C(O)=O.N>>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:20]3[C:19]([NH:21][C@H:22]([C:24]4[N:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:28](=[O:36])[C:27]5=[C:37]([CH3:40])[CH:38]=[CH:39][N:26]5[N:25]=4)[CH3:23])=[N:18][CH:17]=[N:16][C:15]=3[NH:14][CH:13]=2)[CH:7]=1)(=[O:5])=[O:4]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 131736193(S)-N-Methyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzenesulfonamide

Product 1

HCID 90102861(S)-N-Methyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzenesulfonamideYield 76.6%

Procedure

(S)—N-Methyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzenesulfonamide (76 mg, 0.08 mmol) was treated with trifluoroacetic acid (1.52 ml, 18.73 mmol) and a solution of ammonia (7N in methanol, 1.52 ml, 10.64 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (0% to 15% dichloromethane-2-propanol) to obtain 34 mg (71% yield) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 15% dichloromethane-2-propanol)

Sources & evidence

ORD record
ord-be69afe80b0e4aa6867fe1b4afc9c394
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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