HCID 178418361, compound → HCID 178480423, compound

HRID 2274426Notes

Reaction equation

HRID 2274426 reaction equation
[F:1][C:2]1[C:24]([N:25]2[CH2:31][CH2:30][CH2:29][N:28]([CH3:32])[CH2:27][CH2:26]2)=[CH:23][C:5]2[NH:6][C:7]([C:9]3[C:13]([N+:14]([O-])=O)=[CH:12][N:11]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][O:18]4)[N:10]=3)=[N:8][C:4]=2[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[C:24]([N:25]2[CH2:31][CH2:30][CH2:29][N:28]([CH3:32])[CH2:27][CH2:26]2)=[CH:23][C:5]2[NH:6][C:7]([C:9]3[C:13]([NH2:14])=[CH:12][N:11]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][O:18]4)[N:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178480424HCID 178480424, compound

Product 1

HCID 178480423HCID 178480423, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 11.9 g of 5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzimidazole in 260 mL of methanol and 1.2 g of palladium-on-charcoal is hydrogenated under 1 bar of hydrogen pressure at ambient temperature for 18 hours. The reaction medium is filtered through celite and the filtrate is concentrated under reduced pressure in a rotary evaporator. 10.9 g of 3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-ylamine are obtained in the form of a brown powder. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.43 to 2.17 (m, 8H); 2.33 (s, 3H); 2.64 (m, 2H); 2.73 (m, 2H); from 3.20 to 3.40 (m masked, 4H); 3.62 (m, 1H); 3.95 (m, 1H); 4.92 (broad s, 2H); 5.31 (dd, J=2.5 and 10.0 Hz, 1H); from 6.91 to 7.36 (m, 2H); 7.31 (s, 1H); 12.4 (broad m, 1H). ES mass spectrum: m/z=414: MH+ (base peak)—m/z=330: (MH−C5H8O)+

Workup

  1. filtrationThe reaction medium is filtered through celite
  2. concentrationthe filtrate is concentrated under reduced pressure in a rotary evaporator

Sources & evidence

ORD record
ord-a75df38e75114010a8a40ddb33e599d6
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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