4-bromo-1-(3-hydroxypropyl)-1H-pyrazole-5-carbonitrile → 3-amino-6-[5-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

HRID 2279859Notes

Reaction equation

HRID 2279859 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]([CH2:52][CH2:53][CH2:54][OH:55])[C:49]=1[C:50]#[N:51]>>[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]([CH2:52][CH2:53][CH2:54][OH:55])[C:49]=2[C:50]#[N:51])=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 678125994-bromo-1-(3-hydroxypropyl)-1H-pyrazole-5-carbonitrile2×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 866977963-amino-6-[5-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamideYield 29.3%

Procedure

Prepared analogously to 3C using 3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (Compound 48D, 475.3 mg, 1.715 mmol) and 4-bromo-1-(3-hydroxypropyl)-1H-pyrazole-5-carbonitrile (Compound 52D, 434 mg, 1.89 mmol) to afford 151 mg of the title compound (29%). 1H NMR (400 MHz, CD3OD) δ 8.08 (s, 1H), 7.63 (d, J=8.6 Hz, 1H), 7.21 (d, J=8.8 Hz, 1H), 4.47 (t, J=7.1 Hz, 2H), 3.60 (t, J=6.1 Hz, 2H), 2.94 (s, 3H), 2.15 (quin, J=6.6 Hz, 2H). MS (ESI): m/z=301.24 [M+H]+. UPLC: tR=0.79 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-b629f259f71d4dac82ee78d10e55d115
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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