(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 852956Notes

Reaction equation

HRID 852956 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-e9a5801045ab4a7dadb599f28f457a1c
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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