4-Fluorobenzoyl chloride → HCID 46862574, compound

HRID 242465Notes

Reaction equation

HRID 242465 reaction equation
F[C:2]1[CH:3]=[C:4]([C:9]2[C:13]3[CH2:14][NH:15][CH2:16][CH2:17][C:12]=3[N:11]([C:18]([NH:20][C@@H:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:22]([NH:24][CH3:25])=[O:23])=[O:19])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].FC1C=CC(C(Cl)=O)=CC=1.FC1C=C(C2C3CN(C(OC(C)(C)C)=O)CCC=3NN=2)C=CC=1F>>[CH3:27][C:26]([CH3:29])([CH3:28])[C@H:21]([NH:20][C:18]([N:11]1[C:12]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]=2[C:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[CH:2][CH:3]=2)=[N:10]1)=[O:19])[C:22]([NH:24][CH3:25])=[O:23]

Participants

4

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 46862572HCID 46862572, compoundHCID 59345327tert-butyl 3-(3,4-difluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate

Product 1

HCID 46862574HCID 46862574, compound

Procedure

Compound 53 was prepared according to the procedure described for the synthesis of compound 52 by replacing 3,4-difluorobenzoyl chloride with 4-fluorobenzoyl chloride in the synthesis of intermediate 15. 1H NMR (CDCl3) δ 7.96 (d, J=9.5 Hz, 1H), 7.65-7.69 (m, 2H), 7.10-7.15 (m, 2H), 6.27 (br, 1H), 4.18 (d, J=9.4 Hz, 1H), 4.02 (s, 2H), 3.05-3.15 (m, 4H), 2.85 (d, J=4.8 Hz, 3H), 1.10 (s, 9H). LCMS (+ESI) m/z=388.2 [M+H]+.

Sources & evidence

ORD record
ord-2ddbcddc058a4888b70a44ea7dfa676d
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Reaction notes

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