Diisopropylethylamine → (R)-N,N-dimethyl-6-(methyl(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)amino)pyridine-3-sulfonamide

HRID 527944

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:23][NH:24][C@@H:25]1[CH2:29][CH2:28][N:27]([C:30]2[C:31]3[CH:38]=[CH:37][N:36]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:32]=3[N:33]=[CH:34][N:35]=2)[CH2:26]1>CN1C(=O)CCC1.CCOC(C)=O>[CH3:12][N:11]([CH3:13])[S:8]([C:5]1[CH:6]=[N:7][C:2]([N:24]([CH3:23])[C@@H:25]2[CH2:29][CH2:28][N:27]([C:30]3[C:31]4[CH:38]=[CH:37][N:36]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:32]=4[N:33]=[CH:34][N:35]=3)[CH2:26]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 6-chloro-N,N-dimethylpyridine-3-sulfonamide (1 mmol) and DIPEA (2.5 mmol) in NMP (2 mL) was added (R)—N-methyl-1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine (0.5 mmol). The reaction mixture was stirred at 200° C. for 60 minutes in microwave reactor. After cooling to room temperature, the mixture was diluted with EtOAc, washed with brine, dried, filtered, and concentrated. The residue was purified by chromatography with MeOH/H2O to give the title compound in yellow in 8% yield.

Workup

temperatureAfter cooling to room temperature
washwashed with brine
customdried
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography with MeOH/H2O

Sources & evidence

ORD record: ord-be4699431d184566942e8e86427920cb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346810B2

Linked notes

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