Potassium Carbonate → HCID 57829742, compound

HRID 1855449Notes

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

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 47376282-[(2-chloropyrimidin-4-yl)amino]ethanol

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

Product 1

HCID 57829742HCID 57829742, compoundYield 23%

Procedure

Prepared in analogy to example 81b) from 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine and 2-(2-chloro-pyrimidin-4-ylamino)-ethanol, using potassium carbonate as a base. The title compound was isolated as a slightly orange solid in a yield of 23%. MS ISP (m/e): 341.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.14 (s, 1H), 7.91 (s broad, 1H), 7.82 (d broad, 1H), 7.63 (s, 1H), 7.33 (d broad, 1H), 7.25 (s broad, 1H), 7.15 (d, 1H), 7.01 (s, 1H), 6.00 (d, 1H), 4.74 (t, 1H), 3.78 (s, 3H), 3.55 (qa, 2H), 3.50-3.35 (m, 2H), 2.14 (s, 3H).

Sources & evidence

ORD record: ord-3b2a0ee60d80434988d67cc5ded2ec94
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962834B2

Reaction notes

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