3-Dimethylamino-1-(3-pyridyl)-2-propen-1-one → 4-(4-(Pyridin-3-yl)pyrimidin-2-ylamino)benzoic acid

HRID 416283

Reaction equation

HRID 416283 reaction equation
N1C=CN=CC=1C1C=CN=[C:9]([NH:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18](C(O)=O)=[CH:17][CH:16]=2)N=1.[NH:24]([C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1)[C:25]([NH2:27])=[NH:26].CN(/C=C/C(C1C=NC=CN=1)=O)C.CN(C)/C=C/C(C1C=NC=CC=1)=O>>[N:13]1[CH:9]=[CH:17][CH:16]=[C:15]([C:23]2[CH:22]=[CH:18][N:27]=[C:25]([NH:24][C:28]3[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=3)[N:26]=2)[CH:14]=1

Participants

5

Reactant 4

HCID 53691653-Dimethylamino-1-(3-pyridyl)-2-propen-1-oneHCID 5825354(E)-3-(Dimethylamino)-1-(pyrazin-2-YL)prop-2-EN-1-oneHCID 666221674-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acidHCID 178512548HCID 178512548, compound

Product 1

HCID 143469704-(4-(Pyridin-3-yl)pyrimidin-2-ylamino)benzoic acid

Procedure

Title compound was prepared according to the procedure described for the synthesis of compound 25a (scheme 6, step 3) replacing the guanindine 24 by 4-guanidinobenzoic acid (344) (Zlatoidsky P., Maliar T. Eur. J. Med. Chem Chim. Ther.; 1996, 31, 895-900) and (E)-3-(dimethylamino)-1-(pyrazin-2-yl)-prop-2-en-1-one (23a) by (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (345) (Zimmermann J., Buchdunger E., et al. Bioorg. Med. Chem. Lett., 1996, 6, 1221-1226). Yield of the product 28%. MS (m/z): 292.29 (calc) 293.1 (MH+) (found).

Sources & evidence

ORD record
ord-aee82466963b472296b51e3e048c19ac
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Linked notes

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