5-Fluoro-o-toluidine → HCID 57955524, compound

HRID 914225Notes

Reaction equation

HRID 914225 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]([F:19])([F:18])[CH2:9][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:30])=[C:27]([CH:29]=1)[NH2:28]>Cl.CC(O)C>[CH:13]1([N:10]2[CH2:9][C:8]([F:19])([F:18])[C:7](=[O:20])[N:6]([CH3:21])[C:5]3[CH:4]=[N:3][C:2]([NH:28][C:27]4[CH:29]=[C:23]([F:22])[CH:24]=[CH:25][C:26]=4[CH3:30])=[N:12][C:11]2=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 677745-Fluoro-o-toluidineHCID 579555742-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[4,5-B][1,4]diazepin-6(7H)-one

Product 1

HCID 57955524HCID 57955524, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

2-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[5,4-b][1,4]diazepin-6(7H)-one (100 mg, 0.32 mmol), 5-fluoro-2-methylaniline (60 mg, 0.48 mmol), i-PrOH (2 mL) and conc. HCl (5 drops) were heated to 100° C. overnight to give the title compound. The final compound was purified by reverse phase HPLC and basified to give the free base (50 mg, 39%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40-1.96 (m, 9H) 2.22 (s, 3H) 3.99 (t, J=14 Hz, 2H) 4.62 (t, J=8 Hz, 1H) 6.81 (td, J=8, 3 Hz, 1H) 7.19 (t, J=8 Hz, 1H) 7.58 (dd, J=12, 3 Hz, 1H) 8.20 (s, 1H) 8.57 (s, 1H). [M+H] calc'd for C20H22F3N5O, 406. found 406.

Sources & evidence

ORD record
ord-46f86c980c934fcd86c7ffb3934d78d7
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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