Dimethylsulphamoyl chloride → N'-[3-Methoxy-5-(4-{[(1S)-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]-N,N-dimethylsulfamide

HRID 1052572Notes

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.[CH3:47][N:48]([CH3:53])[S:49](Cl)(=[O:51])=[O:50]>N1C=CC=CC=1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([NH:1][S:49]([N:48]([CH3:53])[CH3:47])(=[O:51])=[O:50])[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 dimethylsulfamoyl chloride (25 μL, 0.23 mmol) and 200 μL pyridine according to the method described in Preparation 15b but stirring at 45° C. during 48 h. The residue was purified using SP1® Purification System (0% to 100% hexane-ethyl acetate) to obtain 30 mg (44% yield, 85% purity) of the title compound.

Workup

customThe residue was purified
customSP1® Purification System (0% to 100% hexane-ethyl acetate)

Sources & evidence

ORD record: ord-ea84c5d9f3e441b9bbccc95ab93dadb9
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

Loading…