1-(3-Benzyloxy-2,2-difluoropropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-amino-6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-1H-pyrazol-4-yl}-N-methylpyridine-2-carboxamide

HRID 2279880Notes

Reaction equation

HRID 2279880 reaction equation
NC1C=CC(C2C=NN(CCCO)C=2)=CC=1C(N(CC)CC)=O.[NH2:24][C:25]1[C:26]([C:32]([NH:34][CH3:35])=[O:33])=[N:27][C:28](Br)=[CH:29][CH:30]=1.[CH2:36]([O:43][CH2:44][C:45]([F:62])([F:61])[CH2:46][N:47]1[CH:51]=[C:50](B2OC(C)(C)C(C)(C)O2)[CH:49]=[N:48]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[NH2:24][C:25]1[C:26]([C:32]([NH:34][CH3:35])=[O:33])=[N:27][C:28]([C:50]2[CH:49]=[N:48][N:47]([CH2:46][C:45]([F:62])([F:61])[CH2:44][O:43][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:51]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 678139791-(3-Benzyloxy-2,2-difluoropropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamideHCID 866976863-Amino-6-bromo-N-methylpicolinamide2×

Product 1

HCID 866978193-amino-6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-1H-pyrazol-4-yl}-N-methylpyridine-2-carboxamideYield 64%

Procedure

Prepared analogously to Compound 3C using 3-amino-6-bromo-N-methylpyridine-2-carboxamide (Compound 6D, 359 mg, 1.56 mmol) and 1-[3-(benzyloxy)-2,2-difluoropropyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 59E, 650 mg, 1.72 mmol) to afford 398 mg of the title compound (64%). MS (ESI): m/z=402.16 [M+H]+. UPLC: tR=0.93 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-76babc91a5744f71a6c2be74dacb930f
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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