HCID 89501214, compound → HCID 117777649, compound

HRID 64146Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([C:24]4[N:25]=[N:26][N:27]([CH:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)[CH:28]=4)[CH:23]=[C:18]3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:36]C(=O)C)[CH:10]=1>Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([C:24]4[N:25]=[N:26][N:27]([CH:29]5[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]5)[CH:28]=4)[CH:23]=[C:18]3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH2:36])[CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The compound of Example 181 (0.4 g, 0.757 mmol) was added to aqueous 6 N HCl (10 ml) at 0° C. and the mixture was stirred at 70° C. for 3 h. The mixture was quenched with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate and the residue was purified by column chromatography (60-120 silica gel, 10% methanol in DCM) to give the product in 30% yield (0.11 g). LC-MS (ESI): Calculated mass: 486.52; Observed mass: 487.3 [M+H]+ (rt: 0.22 min).

Workup

customThe mixture was quenched with saturated aqueous sodium bicarbonate solution
extractionextracted with ethyl acetate (3×50 ml)
washThe combined organic layer was washed with water, brine
dry with materialdried over sodium sulphate
customthe residue was purified by column chromatography (60-120 silica gel, 10% methanol in DCM)
customto give the product in 30% yield (0.11 g)
custom487.3 [M+H]+ (rt: 0.22 min)

Sources & evidence

ORD record: ord-ce74f54f6cda4a3da3ca2d52a31475e8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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