Triethylamine → (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

HRID 1052627Notes

Reaction equation

HRID 1052627 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[O:45]1[CH2:50][CH2:49][CH:48]([CH2:51][S:52](Cl)(=[O:54])=[O:53])[CH2:47][CH2:46]1.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:36][C:33]1[CH:34]=[CH:35][N:22]2[C:23]=1[C:24](=[O:32])[N:25]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]([C@@H:18]([NH:17][C:15]1[C:16]3[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:1][S:52]([CH2:51][CH:48]5[CH2:49][CH2:50][O:45][CH2:46][CH2:47]5)(=[O:54])=[O:53])[CH:7]=4)=[CH:9][N:10]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:44])[CH3:43])[C:11]=3[N:12]=[CH:13][N:14]=1)[CH3:19])=[N:21]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18348392(Oxan-4-yl)methanesulfonyl chlorideHCID 131736241(S)-2-(1-((5-(2-Aminopyridin-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 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)methanesulfonamideYield 54.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-2-(1-((5-(2-Aminopyridin-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (80 mg, 0.13 mmol) was treated with (tetrahydro-2H-pyran-4-yl)methanesulfonyl chloride (26 mg, 0.13 mmol) and triethylamine (36 μl, 0.26 mmol) in pyridine (2 ml) according to the method described in Preparation 15b. The residue was purified using SP1® Purification System (hexane-ethyl acetate) to give 55 mg (53% yield) of the title compound. Purity 98%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e3f8cc946bbf47ccb13ca81edb6c5c9c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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