Hydrochloric Acid → 4-[4-(1H-Pyrazol-4-yl)-phenyl]-1,2,3,4,5,6-hexahydro-[4,4']bipyridinyl

HRID 45563Notes

Reaction equation

HRID 45563 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:20]2[CH:25]=[CH:24][C:23](Cl)=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[N:37][NH:38][CH:39]=2)O1.Cl>O1CCOCC1>[NH:37]1[CH:36]=[C:35]([C:23]2[CH:22]=[CH:21][C:20]([C:11]3([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:25][CH:24]=2)[CH:39]=[N:38]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 593319434-(4-Chloro-phenyl)-3,4,5,6-tetrahydro-2H-[4,4']bipyridinyl-1-carboxylic acid tert-butyl ester

Product 1

HCID 111974734-[4-(1H-Pyrazol-4-yl)-phenyl]-1,2,3,4,5,6-hexahydro-[4,4']bipyridinyl

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4-Chloro-phenyl)-3,4,5,6-tetrahydro-2H-[4,4′]bipyridinyl-1-carboxylic acid tert-butyl ester was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole following the procedure set out in Example 1, followed by treatment with 4M HCl in dioxane, to obtain the title compound. LCMS (PS-B4) Rt 4.28 min [M+H]+ 305. 1H NMR (Me-d3-OD) δ 2.76 (2H, br.t), 3.01 (2H, br.d), 3.24 (2H, br.t), 3.39 (2H, br.d), 7.58 (2H, d), 7.76 (2H, d), 8.17 (2H, d), 8.37 (2H, s), 8.82 (2H, d).

Sources & evidence

ORD record
ord-ac3f9dc3e3ef4675a6885911707f6b02
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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