Ammonia → (S)-N-(4-(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)pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)methanesulfonamide

HRID 1052840Notes

Reaction equation

HRID 1052840 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]([NH:36][S:37]([CH2:40][CH:41]5[CH2:46][CH2:45][O:44][CH2:43][CH2:42]5)(=[O:39])=[O:38])[CH:31]=4)=[CH:28][N:27](COCC[Si](C)(C)C)[C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2.FC(F)(F)C(O)=O.N>>[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]([NH:36][S:37]([CH2:40][CH:41]5[CH2:42][CH2:43][O:44][CH2:45][CH2:46]5)(=[O:38])=[O:39])[CH:31]=4)=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 131736242(S)-N-(4-(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)pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)methanesulfonamide

Product 1

HCID 90102604(S)-N-(4-(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)pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)methanesulfonamideYield 11.2%

Procedure

(S)—N-(4-(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)pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)methanesulfonamide (55 mg, 0.07 mmol) was treated with trifluoroacetic acid (2 ml, 26 mmol) and a solution of ammonia (7N in methanol, 2 ml, 91 mmol) according to the method described in Example 27 to give 5 mg (11% yield) of the title compound. Purity 99%.

Sources & evidence

ORD record
ord-c5f2cb44c98b4cadbca59c3fb37b908e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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