1-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehyde → HCID 178422621, compound

HRID 1518155Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

1-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehyde (167 mg, 1.00 mmol, as prepared in Example 19, step B) was placed in a 25 mL round-bottom flask equipped with a magnetic stir bar. 2′-Fluoro-5-methyl-biphenyl-3,4-diamine (218 mg, 1.01 mmol, as prepared in the previous step) was added as a solution in EtOH (10 mL). The flask was fitted with a reflux condenser (top open to air), and the mixture was heated to 80° C. for 6 h. The cooled mixture was concentrated under reduced pressure. The residue was purified by column chromatography using a 40-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0:1 to 3:7, v/v over 30 min, yielding 159 mg (44%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 7.57 (br. s., 1H), 7.50 (td, J=7.8, 1.9 Hz, 1H), 7.31-7.37 (m, 1H), 7.08-7.28 (m, 4H), 2.64 (s, 3H), 2.31 (s, 2H), 1.69-1.89 (m, 6H), 1.47-1.64 (m, 4H).

Workup

customequipped with a magnetic stir bar
customThe flask was fitted with a reflux condenser (top open to air)
concentrationThe cooled mixture was concentrated under reduced pressure
customThe residue was purified by column chromatography
washeluting with EtOAc/hexanes, 0:1 to 3:7, v/v over 30 min

Sources & evidence

ORD record: ord-de9eea9016b841238a7c9faa11f49a5c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232409B2

Reaction notes

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