Sodium Carbonate → (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol

HRID 74951Notes

Reaction equation

HRID 74951 reaction equation
N[C@H:2]1[CH2:7][CH2:6]CC[C@@H:3]1[C:8](O)=[O:9].CC[N:13](C(C)C)C(C)C.[C:20]([O-:23])([O-])=O.[Na+].[Na+].ClC1C=C2C(B3OC(C)(C)C(C)(C)O3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.[Cl:55][C:56]1[CH:57]=[C:58]2[C:64]([C:65]3[N:70]=[C:69](S(C)=O)[C:68]([F:74])=[CH:67][N:66]=3)=[CH:63][N:62](S(C3C=CC(C)=CC=3)(=O)=O)[C:59]2=[N:60][CH:61]=1>CCO.C1COCC1.C1COCC1.CC#N>[Cl:55][C:56]1[CH:57]=[C:58]2[C:64]([C:65]3[N:70]=[C:69]([NH:13][C:20]4([OH:23])[CH2:6][CH2:7][CH2:2][CH2:3][CH:8]4[OH:9])[C:68]([F:74])=[CH:67][N:66]=3)=[CH:63][NH:62][C:59]2=[N:60][CH:61]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 7128323(1S,2S)-2-Aminocyclohexanecarboxylic AcidHCID 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]pyridine

Product 1

HCID 86762729(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

(1S,2S)-2-aminocyclohexanecarboxylic acid, iPr2NEt, Na2CO3, THF—CH3CN (3:1), 135° C. microwave; (b) 1N LiOH, THF, microwave, 120° C.; (c) 4NHCl-dioxane, EtOH, 70° C.

Sources & evidence

ORD record
ord-e79844658335406a8e421738f1a78092
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

Loading…