Sodium hydride → (1S,2S)-isopropyl 2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexanecarboxylate

HRID 74953Notes

Reaction equation

HRID 74953 reaction equation
[H-].[Na+].IC.[CH3:5]N(C=O)C.Cl[C:11]1[CH:12]=[C:13]2C(B3OC(C)(C)C(C)(C)O3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)[C:14]2=[N:15][CH:16]=1.[Cl:39][C:40]1[CH:41]=[C:42]2[C:48]([C:49]3[N:54]=[C:53](S(C)=O)[C:52]([F:58])=[CH:51][N:50]=3)=[CH:47][N:46](S(C3C=CC(C)=CC=3)(=O)=O)[C:43]2=[N:44][CH:45]=1.[CH2:69]1[CH2:73][O:72][CH2:71][CH2:70]1.[OH2:74]>CCO.N1C=CC=CC=1>[Cl:39][C:40]1[CH:41]=[C:42]2[C:48]([C:49]3[N:54]=[C:53]([NH:15][C@H:14]4[CH2:13][CH2:12][CH2:11][CH2:16][C@@H:69]4[C:73]([O:72][CH:71]([CH3:70])[CH3:5])=[O:74])[C:52]([F:58])=[CH:51][N:50]=3)=[CH:47][NH:46][C:43]2=[N:44][CH:45]=1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 21881883Oxolane--water (1/1)HCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridineHCID 86587335iodomethane DMF

Product 1

HCID 68007808(1S,2S)-isopropyl 2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

NaH, iodomethane DMF; (b) NH2OH—HCl, pyridine, EtOH; (c) Al (Hg), THF—H2O (4:1).

Sources & evidence

ORD record
ord-06e335c5f9c94a57988e7e63af2864e7
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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