HCID 71571988, compound → HCID 71525317, compound

HRID 2276801Notes

Reaction equation

HRID 2276801 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([CH:27]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[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]=2)=[CH:10][CH:9]=1.[Cl:29][C:30]1[CH:51]=[CH:50][C:33]([O:34][C:35]2[CH:40]=[CH:39][C:38]([CH:41]3[BH:45][C:44]([CH3:47])([CH3:46])[C:43]([CH3:49])([CH3:48])[O:42]3)=[CH:37][CH:36]=2)=[C:32]([F:52])[CH:31]=1>>[Cl:29][C:3]1[CH:2]=[CH:27][C:6]([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)=[C:5]([F:28])[CH:4]=1.[Cl:29][C:30]1[CH:51]=[CH:50][C:33]([O:34][C:35]2[CH:36]=[CH:37][C:38]([CH:41]3[BH:45][C:44]([CH3:46])([CH3:47])[C:43]([CH3:48])([CH3:49])[O:42]3)=[CH:39][CH:40]=2)=[C:32]([F:52])[CH:31]=1

Participants

4

Reactant 2

HCID 71571988HCID 71571988, compoundHCID 178421689HCID 178421689, compound

Product 2

HCID 71525317HCID 71525317, compoundHCID 178421689HCID 178421689, compound

Procedure

(R)-2-(4-(4-chloro-2-fluorophenoxy)phenyl)-6-(1,2-dihydroxyethyl) pyrimidine-4-carboxamide (Compound Example No. 9) was prepared in a similar fashion to (R)-2-(4-(5-chloro-2-fluorophenoxy)phenyl)-6-(1,2-dihydroxyethyl) pyrimidine-4-carboxamide (Compound Example No. 7) using 2-(4-(4-chloro-2-fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,3-dioxaborolane (6) instead of 2-(4-(5-chloro-2-fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,3-dioxaborolane (14). 1H NMR (400 MHz, CD3OD): 8.49 (2H, d, J=8.8 Hz), 8.03 (1H, s), 7.30 (1H, dd, J=2.8, 10 Hz), 7.18-7.10 (2H, m), 6.96 (2H, d, J=9.2 Hz), 4.73 (1H, dd, J=3.2, 5.6 Hz), 3.89 (1H, dd, J=3.6, 11 Hz), 3.75 (1H, dd, J=6.0, 11 Hz); LC/MS: m/z=404[M+H]+. Compound 6 was prepared according to Scheme 1 in Example 1.

Sources & evidence

ORD record
ord-27147c7dffa444e388a5496b99b6cecf
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

Loading…