4-Morpholinobenzaldehyde → HCID 178421259, compound

HRID 592046Notes

Reaction equation

[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C:10]23[C:16]([CH3:18])([CH3:17])[C:13]([CH3:19])([CH2:14][CH2:15]2)[C:12](=[O:20])[CH2:11]3)[C:5]([Cl:21])=[CH:4][N:3]=1.[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.C([O-])(=O)C.[NH4+]>CCO>[Cl:21][C:5]1[C:6]([NH:9][C:10]23[C:16]([CH3:17])([CH3:18])[C:13]([CH3:19])([CH2:14][CH2:15]2)[C:12](=[O:20])[CH2:11]3)=[C:7]2[N:8]=[C:32]([C:31]3[CH:30]=[CH:29][C:28]([N:25]4[CH2:26][CH2:27][O:22][CH2:23][CH2:24]4)=[CH:35][CH:34]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-(2,3-diamino-5-chloropyridin-4-ylamino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (10) (300 mg, 0.971 mmol), 4-morpholinobenzaldehyde (167 mg, 0.873 mmol) were taken in EtOH (15 ml) to which ammonium acetate (112 mg) was added and the reaction mixture was heated at 70° C. for 48 h. Crude LCMS showed the desired product along with trace of starting material. The reaction mixture was allowed to come to rt and the precipitated was filtered and washed well with ethanol to afford the desired product (466 mg, 23%) as a yellow solid. NMR: δ (1H, 400M Hz, DMSO-d6): 0.91 (3H, s), 0.92 (3H, s), 1.09 (3H, s), 1.40-1.50 (1H, m), 1.70-1.80 (2H, m), 2.40-2.60 (1H, m), 3.00-3.10 (1H, m), 3.20-3.30 (4H, m), 3.72-3.80 (5H, m), 5.37 (1H, s), 7.09 (2H, d, J=8.8 Hz), 7.99 (2H, d, J=8.8 Hz), 8.02 (1H, s), 13.15 (1H, s). LCMS (254 nm): [M+H]+ 480.20 (95.88%) HPLC: 95.55% (220 nm)

Workup

additionwas added

Sources & evidence

ORD record: ord-50d8032559fb446a92cbedd1184794e9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

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