2-Bromopentane → N-(1-methylbutyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

HRID 589981Notes

Reaction equation

C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:28])(=[O:27])[NH2:26])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:36]([CH2:38][CH2:39][CH3:40])[CH3:37]>CN(C=O)C>[CH3:37][CH:36]([NH:26][S:25]([N:20]1[C:21]2([CH2:22][CH2:23]2)[CH2:24][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:18][CH2:19]1)(=[O:27])=[O:28])[CH2:38][CH2:39][CH3:40]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 2) (0.049 mmol) was dissolved in dry DMF (1 mL) and added Cs2CO3 (0.147 mmol) and 2-bromopentane (0.074 mmol). Stirred at 60° C. for 16 h and then filtered through a syringe filter. The obtained filtrate was added 2,2,2-trifluoroethanol (1 mL) and heated to 100° C. for 1 h. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

filtrationfiltered through a syringe
filtrationfilter
additionThe obtained filtrate was added 2,2,2-trifluoroethanol (1 mL)
temperatureheated to 100° C. for 1 h
customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record: ord-c85f1fc072c4458c9434a8b32f7ccb7b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233964B2

Reaction notes

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