3-(4-Iodo-3-methoxy-pyrazol-1-yl)-propan-1-ol → 3-amino-6-[1-(3-hydroxypropyl)-3-methoxy-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

HRID 2279843Notes

Reaction equation

HRID 2279843 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.I[C:45]1[C:46]([O:54][CH3:55])=[N:47][N:48]([CH2:50][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[C:46]([O:54][CH3:55])=[N:47][N:48]([CH2:50][CH2:51][CH2:52][OH:53])[CH:49]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 678140643-(4-Iodo-3-methoxy-pyrazol-1-yl)-propan-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 866977803-amino-6-[1-(3-hydroxypropyl)-3-methoxy-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamideYield 30%

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, 500 mg, 2 mmol) and 3-(4-iodo-3-methoxy-pyrazol-1-yl)-propan-1-ol (Compound 48E, 600 mg, 2.18 mmol) to afford 177 mg of the title compound (30%). 1H NMR (400 MHz, CD3OD) δ 8.13 (s, 1H), 7.67 (d, J=8.8 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 4.11 (t, J=6.8 Hz, 2H), 3.98 (s, 3H), 3.57 (t, J=6.2 Hz, 2H), 2.93 (s, 3H), 2.05 (t, J=6.4 Hz, 2H). MS (ESI): m/z=306.24 [M+H]+. UPLC: tR=0.75 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-01a4d5d294ed44e9963beaf36897668d
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…