P-Anisidine → HCID 67008043, compound

HRID 1013873Notes

Reaction equation

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

Participants

Reactant 3

HCID 7732P-Anisidine

HCID 21584188Chloroform methanol

HCID 57625951N-(4-chloro-9H-pyrimido[4,5-b]indol-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 67008043HCID 67008043, compoundYield 51%

Procedure

Using the general procedure described above, the reaction of 6 (80 mg, 0.26 mmol) and 4-methoxyaniline (244 mg, 1.98 mmol) was run for 18 hours, to provide 52 mg of 8 as a white solid in 51% yield, TLC Rf 0.55 (chloroform-methanol 15:1); mp 266.8-267° C.; 1H NMR (DMSO-d6) δ 1.23 (s, 9H, C(CH3)3), 3.75 (s, 3H, OCH3), 6.88-8.26 (m, 8H, Ar—H), 8.55 (s, 1H, 4-NH, exch), 9.41 (s, 1H, 2-NH, exch), 11.79 (s, 1H, 9-NH, exch). Anal. Calculated (C22H23N5O2, 0.4 H2O): C, 66.61; H, 6.04; N, 17.65. Found: C, 66.61; H, 6.00; N, 17.37.

Sources & evidence

ORD record: ord-3605249424b141ffb35321063b451609
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982035B2

Reaction notes

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