Pyridine → (S)-N-(3-Methoxy-5-(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)phenyl)methanesulfonamide

HRID 1052564Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[C:18]3[C:17]([NH:19][C@H:20]([C:22]4[N:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:26](=[O:34])[C:25]5=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]5[N:23]=4)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=3[N:12]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:11]=2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.N1C=CC=CC=1.[CH3:53][S:54](Cl)(=[O:56])=[O:55]>O1CCCC1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([NH:1][S:54]([CH3:53])(=[O:56])=[O:55])[CH:3]=[C:4]([C:10]2[C:18]3[C:17]([NH:19][C@H:20]([C:22]4[N:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:26](=[O:34])[C:25]5=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]5[N:23]=4)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=3[N:12]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:11]=2)[CH:5]=1

Participants

Conditions

Temperature: 45 °C

Procedure

(S)-2-(1-((5-(3-Amino-5-methoxyphenyl)-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 (50 mg, 0.08 mmol) was treated with pyridine (22 μl, 0.27 mmol), methanesulfonyl chloride (18 μl, 0.23 mmol) and 0.75 ml tetrahydrofuran as a solvent according to the method described in Preparation 175 but heating at 45° C. during 48 h. The residue was purified using SP1® Purification System (0% to 70% hexane-ethyl acetate) to obtain 42 mg (67% yield, 89% purity) of the title compound.

Workup

customdescribed in Preparation 175
customThe residue was purified
customSP1® Purification System (0% to 70% hexane-ethyl acetate)

Sources & evidence

ORD record: ord-c548b9f42d934dc5918ec3b75896e074
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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