Potassium Carbonate → HCID 57829799, compound

HRID 1855444Notes

Reaction equation

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

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

HCID 86633625HCID 86633625, compound

Product 1

HCID 57829799HCID 57829799, compoundYield 79%

Procedure

Prepared in analogy to example 81b) from 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine and [(2-chloro-6-methyl-pyrimidin-4-yl)-methyl-amino]acetic acid tert-butyl ester, using potassium carbonate as a base. The title compound was isolated as a slightly yellow foam in a yield of 79%. MS ISP (m/e): 439.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.65 (s broad, 1H), 7.60 (d, 1H), 7.12 (d, 1H), 7.05-6.95 (m, 2H), 6.85 (s, 1H), 5.94 (s, 1H), 3.87 (s, 3H), 3.12 (s broad, 3H), 2.30 (s, 3H), 2.29 (s, 3H), 1.39 (s, 9H).

Sources & evidence

ORD record: ord-072a89e3a7844ab493729efc9974bb72
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962834B2

Reaction notes

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