Ethyl valerate → US10023592, Example 350

HRID 518528

Reaction equation

HRID 518528 reaction equation
[C:1](OCC)(=O)CCCC.ClC1C(CCC)=CN=C([S:20]([CH3:23])(=[O:22])=[O:21])N=1.C(OCC)(=O)CCCCC.C(C1C(Cl)=NC(S(C)(=O)=O)=NC=1)CCC.FC1C=C(F)C=CC=1O[C:53]1[C:54]([C:64]2[CH:65]=[C:66]([O:72][CH3:73])[C:67](=[O:71])[N:68]([CH3:70])[CH:69]=2)=NC(CS(C)(=O)=O)=N[CH:58]=1.CN1C=C(B2OC(C)(C)C(C)(C)O2)C=CC1=O.ClC1C(=O)N(C)C=C(C2C=[C:107](NS(CC)(=O)=O)[CH:108]=[CH:109][C:110]=2[O:111][C:112]2[CH:117]=CC(F)=C[C:113]=2F)C=1>>[CH:109]1([CH2:110][O:111][C:112]2[CH:113]=[C:54]([C:64]3[C:65]4[CH:1]=[CH:73][O:72][C:66]=4[C:67](=[O:71])[N:68]([CH3:70])[CH:69]=3)[CH:53]=[C:58]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:117]=2)[CH2:108][CH2:107]1

Participants

8

Reactant 7

HCID 10882Ethyl valerateHCID 31265Ethyl hexanoateHCID 454801941-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 72550334HCID 72550334, compoundHCID 118021343US10023592, Example 146HCID 1180215584-Chloro-2-methylsulfonyl-5-propylpyrimidineHCID 1180216475-Butyl-4-chloro-2-methylsulfonylpyrimidine

Product 1

HCID 118021484US10023592, Example 350

Procedure

Examples 351-356 in Table 19 were prepared in a similar multi-step manner as Example 300, step 1 wherein either ethyl pentanoate was converted to 4-chloro-2-methylsulfonyl-5-propylpyrimidine or ethyl hexanoate was converted to 5-butyl-4-chloro-2-methylsulfonylpyrimidine which were then each reacted with a) 3-methoxy-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (described in Example 146, step 3), b) the title compound of Example 98, step 1, or c) 3-chloro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (described in Example 134) in a manner similar to Example 152, step 5 to give the title compound.

Sources & evidence

ORD record
ord-958129c3f413483bbff3763589223c5b
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Linked notes

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