2486-69-3 → HCID 25253068, compound

HRID 914175Notes

Reaction equation

HRID 914175 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:16])([CH:14]=[CH2:15])[CH2:8][N:7]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:6]=2[N:22]=1.[NH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=1[O:33][CH3:34]>Cl.CC(O)C>[CH:17]1([N:7]2[CH2:8][C:9]([F:16])([CH:14]=[CH2:15])[C:10](=[O:13])[N:11]([CH3:12])[C:5]3[CH:4]=[N:3][C:2]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=4[O:33][CH3:34])=[N:22][C:6]2=3)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 2880572486-69-3HCID 57955616HCID 57955616, compound

Product 1

HCID 25253068HCID 25253068, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

2-Chloro-9-cyclopentyl-7-fluoro-5-methyl-7-vinyl-8,9-dihydro-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one, 4-amino-3-methoxy benzoic acid (1.2 equivalent), i-PrOH and conc. HCl (30 drops) were heated to 95° C. for 18 hours. A this time the reaction was cooled to room temperature and filtered to reveal the product as a tan solid in good yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51-1.75 (m, 6H) 1.85 (m, 2H) 3.29 (s, 3H) 3.73-3.97 (m, 2H) 3.93 (s, 3H) 4.94 (m, 1H) 5.40-5.54 (m, 2H) 6.05 (m, 1H) 7.48-7.65 (m, 2H) 8.09 (d, J=8.34 Hz, 1H) 8.23 (s, 1H) 9.51 (br. s., 1H). [M+H] calculated for C23H26FN5O4, 456. found 456.

Workup

  1. filtrationfiltered
  2. customin good yield)

Sources & evidence

ORD record
ord-f3c920a1174f44dcb5feaad5ecb05634
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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