Sodium Hydroxide → HCID 58168033, compound

HRID 1029292Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[CH:12]=[CH:13][C:14]([NH:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])=[CH:15][C:10]=2[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-:26].[Na+]>CN(C)C(=O)C>[O:1]=[C:2]1[C:11]2[CH:12]=[CH:13][C:14]([NH:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]([NH2:22])=[O:26])=[CH:15][C:10]=2[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

463 (48 mg, 0.15 mmol) and NaOH (1M, aqueous, 0.73 mL) were suspended in N,N-dimethylacetamide (2 mL), and stirred for 16 h at 100° C. The reaction mixture was purified directly via prep-LC-MS to provide 473 (24 mg, 47% yield) as a white powder. LC-MS (M+H=345, obsd.=345). 1H NMR (400 MHz, DMSO-D6) δ 8.55 (d, J=7.8, 1H), 8.50 (d, J=4.3, 1H), 8.06 (d, J=8.5, 1H), 7.94 (s, 1H), 7.74 (s, 1H), 7.69 (d, J=7.5, 1H), 7.43 (s, 1H), 7.35 (dd, J=7.2, 14.4, 2H), 6.91 (d, J=8.8, 1H), 5.70 (s, 2H).

Workup

customThe reaction mixture was purified directly via prep-LC-MS

Sources & evidence

ORD record: ord-62554bfba8944e38a119b2d2562a164e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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