Sodium Hydroxide → 1-(5-(4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)furo[3,2-d]pyrimidin-2-yl)pyridin-2-yl)urea

HRID 881370Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[O:22][C:21]([CH2:23][N:24]4[CH2:29][CH2:28][N:27]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:26][CH2:25]4)=[CH:20][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=3)[N:12]=2)[CH2:3][CH2:2]1.ClS([N:38]=[C:39]=[O:40])(=O)=O.[OH-].[Na+]>C(#N)C>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:8]3[O:22][C:21]([CH2:23][N:24]4[CH2:25][CH2:26][N:27]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:28][CH2:29]4)=[CH:20][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([NH:19][C:39]([NH2:38])=[O:40])=[N:17][CH:18]=3)[N:12]=2)[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 236 (1.0 eq) in acetonitrile (0.1M) at r.t. was added chlorosulfonyl isocyanate (10 eq) dropwise. The reaction was stirred for 40 minutes, then concentrated. To the residue was added 2N HCl and mixture was heated to 80° C. for 20 minutes. Reaction mixture was allowed to cool down to room temperature, and was neutralized with NaOH 6M. Mixture was then concentrated. The crude product was purified by reverse phase HPLC to give 6 mg of 247. MS (Q1) 517 (M+

Workup

concentrationconcentrated
additionTo the residue was added 2N HCl and mixture
customReaction mixture
temperatureto cool down to room temperature
concentrationMixture was then concentrated
customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-e0411f8f94ac451ba8c1b4fa022a5f75
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993563B2

Reaction notes

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