(E)-3-(Dimethylamino)-1-(pyrazin-2-YL)prop-2-EN-1-one → 4-((4-(2-(Tert-butoxycarbonylamino)-4-methylthiazol-5-yl)-pyrimidin-2-ylamino)methyl)benzoic acid

HRID 416282

Reaction equation

HRID 416282 reaction equation
N1C=CN=CC=1C1C=CN=C([NH:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)N=1.C[N:25](/C=C/C(C1C=NC=CN=1)=O)C.[C:37]([NH:44][C:45]1[S:46][C:47]([C:51](=O)/[CH:52]=[CH:53]/[N:54]([CH3:56])C)=[C:48]([CH3:50])[N:49]=1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>>[C:40]([O:39][C:37]([NH:44][C:45]1[S:46][C:47]([C:51]2[CH:52]=[CH:53][N:54]=[C:56]([NH:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:22][CH:23]=3)[N:25]=2)=[C:48]([CH3:50])[N:49]=1)=[O:38])([CH3:41])([CH3:42])[CH3:43]

Participants

4

Reactant 3

HCID 5825354(E)-3-(Dimethylamino)-1-(pyrazin-2-YL)prop-2-EN-1-oneHCID 58930506(E)-1-[2-(Boc-Amino-)-4-methylthiazol-5-yl]-3-(dimethylamino)prop-2-en-1-oneHCID 666221674-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acid

Product 1

HCID 589304744-((4-(2-(Tert-butoxycarbonylamino)-4-methylthiazol-5-yl)-pyrimidin-2-ylamino)methyl)benzoic acidYield 18%

Procedure

Following the procedure described for the synthesis of the acid 25a (scheme 6, step 3) but substituting enamino ketone 23a for the enamino ketone 338, title compound was obtained in 18% yield and was used for the next steps without further purification. MS (m/z): 441.50 (calc) 442.3 (MH+) (found).

Sources & evidence

ORD record
ord-aeeadea4a66a45d79c56970b509663a4
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Linked notes

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