3-Fluoroaniline → HCID 57955605, compound

HRID 1880995Notes

Reaction equation

HRID 1880995 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]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>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:26][C:25]4[CH:27]=[CH:28][CH:29]=[C:23]([F:22])[CH:24]=4)=[N:12][C:11]2=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 97423-FluoroanilineHCID 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 57955605HCID 57955605, 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), 3-fluoroaniline (54 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, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58-1.96 (m, 8 H) 4.04 (t, J=14 Hz, 2 H) 4.78 (m, 1 H) 6.59-6.87 (m, 1 H) 7.16-7.33 (m, 1 H) 7.38 (d, J=8 Hz, 1 H) 7.79 (d, J=12 Hz, 1 H) 8.26 (s, 1 H) 9.66 (br. s., 1 H). [M+H] calc'd for C19H20F3N5O, 392; found 392.

Sources & evidence

ORD record
ord-2e44a23355254845a7c4d42ef76913a4
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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