3-(4-Bromo-pyrazol-1-yl)-3-methyl-butan-1-ol → 3-amino-6-[1-(4-hydroxy-2-methylbutan-2-yl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

HRID 2279849Notes

Reaction equation

HRID 2279849 reaction equation
NC1C=CC(C2C=NN(CCCO)C=2)=CC=1C(N(CC)CC)=O.[NH2:24][C:25]1[C:26]([C:40]([NH:42][CH3:43])=[O:41])=[N:27][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:30]=1.Br[C:45]1[CH:46]=[N:47][N:48]([C:50]([CH3:55])([CH3:54])[CH2:51][CH2:52][OH:53])[CH:49]=1>>[NH2:24][C:25]1[C:26]([C:40]([NH:42][CH3:43])=[O:41])=[N:27][C:28]([C:45]2[CH:46]=[N:47][N:48]([C:50]([CH3:55])([CH2:51][CH2:52][OH:53])[CH3:54])[CH:49]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 678112743-(4-Bromo-pyrazol-1-yl)-3-methyl-butan-1-ol2×HCID 678189263-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide2×HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 866977873-amino-6-[1-(4-hydroxy-2-methylbutan-2-yl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamideYield 43%

Procedure

Prepared analogously to Compound 3C using 3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (Compound 48D, 649 mg, 2.34 mmol) and 3-(4-bromo-pyrazol-1-yl)-3-methyl-butan-1-ol (Compound 50D, 600 mg, 2.57 mmol) to afford 304 mg of the title compound (43%). 1H NMR (400 MHz, CD3OD) δ 8.34 (d, J=0.5 Hz, 1H), 8.01 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.15 (d, J=8.6 Hz, 1H), 3.40 (t, J=7.2 Hz, 2H), 2.94 (s, 3H), 2.17 (t, J=7.3 Hz, 2H), 1.66 (s, 6H). MS (ESI): m/z=304.26 [M+H]+. UPLC: tR=0.77 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-8a1b87eda39e4365bbee3d4dd707a525
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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