N-Methyl-4-anisidine → HCID 67007902, compound

HRID 1013874Notes

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:31]=[CH:30][C:27]([NH:28][CH3:29])=[CH:26][CH:25]=1.C(Cl)(Cl)Cl.[CH3:36][OH:37]>>[CH3:36][O:37][C:31]1[CH:30]=[C:27]([N:28]([CH3:29])[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:26]=[CH:25][CH:24]=1

Participants

Reactant 3

HCID 22250N-Methyl-4-anisidine

HCID 21584188Chloroform methanol

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

Product 1

HCID 67007902HCID 67007902, compoundYield 45%

Procedure

Using the general procedure described above, the reaction of 6 (180 mg, 0.59 mmol) and 4-methoxy-N-methylaniline (612 mg, 4.46 mmol) was run for 72 hours, to provide 109 mg of 9 as brown crystals in 45% yield, TLC Rf 0.62 (chloroform-methanol 15:1); mp 248.2-249° C.; 1H NMR (DMSO-d6) δ 1.26 (s, 9H, C(CH3)3), 3.61 (s, 3H, OCH3), 3.74 (s, 3H, NCH3), 5.76-7.29 (m, 8H, Ar—H), 9.49 (s, 1H, 2-NH, exch), 11.81 (s, 1H, 9-NH, exch). Anal. Calculated (C23H25N5O2. 0.55 CH3OH): C, 67.16; H, 6.51; N, 16.63. Found: C, 67.33; H, 6.49; N, 16.28.

Sources & evidence

ORD record: ord-678bc4004c374762a0c029640ca9da70
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982035B2

Reaction notes

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