Sodium Carbonate → HCID 178427931, compound

HRID 510923Notes

Reaction equation

HRID 510923 reaction equation
Br[C:2]1[C:3]([O:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[C:4]([CH:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3C2CCCCO2)[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[CH3:37][S:38]([C:41]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=1)(=[O:40])=[O:39].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>>[Cl:9][C:6]1[CH:5]=[C:4]([CH:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][NH:17]3)[CH3:11])[C:3]([O:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[C:2]([C:44]2[CH:45]=[CH:46][C:41]([S:38]([CH3:37])(=[O:40])=[O:39])=[CH:42][CH:43]=2)[C:7]=1[CH3:8]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 86666838HCID 86666838, compound

Product 1

HCID 178427931HCID 178427931, compoundYield 27%

Procedure

The desired compound was prepared according to the procedure of Example 125, step D, using N-{1-[3-bromo-5-chloro-4-methyl-2-(2-morpholin-4-ylethoxy)phenyl]ethyl}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine, [4-(methylsulfonyl)phenyl]boronic acid, and sodium carbonate (instead of potassium carbonate) as the starting materials in 27% yield. LCMS for C27H32ClN6O4S (M+H)+: m/z=571.2. Found: 571.3; 1H NMR (400 MHz, DMSO-d6): δ 12.9 (s, 1H), 8.17-8.07 (m, 3H), 8.00 (d, J=7.9 Hz, 2H), 7.67 (s, 1H), 7.64 (d, J=7.2 Hz, 1H), 7.55 (d, J=7.4 Hz, 1H), 5.80 (s, 1H), 4.15-3.84 (m, 1H), 3.42-3.37 (m, 4H), 3.28 (s, 3H), 2.32-2.25 (m, 2H), 2.17-2.12 (m, 2H), 2.08-2.00 (m, 2H), 1.98 (s, 3H), 1.50 (d, J=6.9 Hz, 3H).

Sources & evidence

ORD record
ord-28c39bd355e242afbfec3ddacf9bba14
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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