HCID 66806437, compound → HCID 71572208, compound

HRID 2276813Notes

Reaction equation

C(C1C=CC([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]([NH2:22])=[O:21])[CH:17]=[C:16]([C@@H:23]([OH:26])[CH2:24][OH:25])[N:15]=3)=[CH:10][CH:9]=2)=CC=1C(F)(F)F)#N.CC1(C)C(C)(C)OB(C2C=CC(O[C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=3)=CC=2)O1>>[OH:26][C@H:23]([C:16]1[N:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=3)=[CH:9][CH:10]=2)[N:19]=[C:18]([C:20]([NH2:22])=[O:21])[CH:17]=1)[CH2:24][OH:25]

Participants

Reactant 2

HCID 66806437HCID 66806437, compound

HCID 71572099HCID 71572099, compound

Product 1

HCID 71572208HCID 71572208, compound

Procedure

(R)-6-(1,2-dihydroxyethyl)-2-(4-(4-(trifluoromethyl)phenoxy)phenyl) pyrimidine-4-carboxamide (Compound Example No. 18) was prepared a similarly to (R)-2-(4-(4-cyano-3-(trifluoromethyl)phenoxy)phenyl)-6-(1,2-dihydroxyethyl) pyrimidine-4-carboxamide (Compound Example No. 12) using 4,4,5,5-tetramethyl-2-(4-(4-(trifluoromethyl)phenoxy)phenyl)-1,3,2-dioxaborolane. 1H NMR (400 MHz, DMSO-d6): 8.75-8.67 (2 H, m), 8.65-8.59 (1 H, m), 8.05-8.01 (1 H, m), 8.01-7.94 (1 H, m), 7.83-7.75 (2 H, m), 7.31-7.22 (4 H, m), 5.84-5.79 (1 H, m), 4.87-4.79 (1 H, m), 4.73-4.67 (1 H, m), 3.86-3.77 (1 H, m), 3.74-3.64 (1 H, m); LC/MS: m/z=420 [M+H]+.

Sources & evidence

ORD record: ord-5a980683e6624cc0965534b01d793a75
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133131B2

Reaction notes

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