HCID 57916409, compound → HCID 60207864, compound

HRID 910264Notes

Reaction equation

HRID 910264 reaction equation
C[N:2](/[CH:4]=[C:5](/[C:10](=O)[CH2:11]OCC)\C(OC)=O)[CH3:3].CN(/C=C(/C(=O)CCCC)\C(OC)=O)C.Cl[C:32]1[C:37]([CH3:38])=[CH:36][N:35]=[C:34]([N:39]2[C:43]([CH2:44][O:45][CH2:46][CH3:47])=[C:42]([C:48]([NH:50][CH2:51][C:52]3[N:56]([CH3:57])[CH:55]=[N:54][CH:53]=3)=[O:49])[CH:41]=[N:40]2)[N:33]=1>>[CH2:46]([O:45][CH2:44][C:43]1[N:39]([C:34]2[N:33]=[C:32]([N:2]3[CH2:4][CH2:5][CH2:10][CH2:11][CH2:3]3)[C:37]([CH3:38])=[CH:36][N:35]=2)[N:40]=[CH:41][C:42]=1[C:48]([NH:50][CH2:51][C:52]1[N:56]([CH3:57])[CH:55]=[N:54][CH:53]=1)=[O:49])[CH3:47]

Participants

4

Reactant 3

HCID 57916409HCID 57916409, compoundHCID 60207865HCID 60207865, compoundHCID 60207866HCID 60207866, compound

Product 1

HCID 60207864HCID 60207864, compound

Procedure

The title compound 99 was prepared by following the synthetic sequence and conditions described in Example 14 and Example 16 with the following modifications. First in Step 2 of Example 14, intermediate D.2 (R2=methyl, R3=H) was treated with (Z)-methyl 2-((dimethylamino)methylene)-4-ethoxy-3-oxobutanoate, instead of (Z)-methyl 2-((dimethylamino)methylene)-3-oxoheptanoate, to give D.3 (R2=methyl, R4=ethoxymethyl). This intermediate D.3 was converted to the corresponding D.5, 1-(4-chloro-5-methylpyrimidin-2-yl)-5-(ethoxymethyl)-N-((1-methyl-1H-imidazol-5-yl)methyl)-1H-pyrazole-4-carboxamide, in three steps (Steps 3-5).

Workup

  1. customto give D.3 (R2=methyl, R4=ethoxymethyl)

Sources & evidence

ORD record
ord-537571a3e7de4b8e8e9c7b3e37b2e0ea
Source dataset
uspto-grants-2011_09
Patent number
US08022061B2

Reaction notes

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