Triethylamine → HCID 59856891, compound

HRID 1174798Notes

Reaction equation

HRID 1174798 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[OH:13][C@@H:14]1[CH2:18][CH2:17][O:16][CH2:15]1.C(N(CC)CC)C.[F:26][C:27]1[CH:47]=[C:46]([S:48]([CH3:51])(=[O:50])=[O:49])[CH:45]=[CH:44][C:28]=1[O:29][C:30]1[C:35]([CH3:36])=[C:34]([O:37][CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[N:33]=[CH:32][N:31]=1>C1COCC1>[O:16]1[CH2:17][CH2:18][C@@H:14]([O:13][C:1]([N:41]2[CH2:42][CH2:43][CH:38]([O:37][C:34]3[C:35]([CH3:36])=[C:30]([O:29][C:28]4[CH:44]=[CH:45][C:46]([S:48]([CH3:51])(=[O:49])=[O:50])=[CH:47][C:27]=4[F:26])[N:31]=[CH:32][N:33]=3)[CH2:39][CH2:40]2)=[O:2])[CH2:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 641512(-)-3-HydroxytetrahydrofuranHCID 672020214-(2-Fluoro-4-methanesulfonyl-phenoxy)-5-methyl-6-(piperidin-4-yloxy)-pyrimidine

Product 1

HCID 59856891HCID 59856891, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,1′-carbonyldiimidazole (54.8 mg, 0.338 mmol) in 1 mL THF was added (R)-(+)-3-hydroxytetrahydrofuran (32 μl, 0.38 mmol). After stirring for 30 minutes at room temperature, 1 mL triethylamine, 1 mL THF, and 4-(2-fluoro-4-methanesulfonyl-phenoxy)-5-methyl-6-(piperidin-4-yloxy)-pyrimidine (70 mg, 0.166 mmol) were added. The resulting mixture was stirred at 60° C. for 48 hours and purified by HPLC to give Compound C177 as a white solid (35.3 mg, 42%). 1H NMR (CDCl3, 400 MHz) δ 1.81-1.88 (m, 2H), 1.96-2.09 (m, 3H), 2.12-2.20 (m, 4H), 3.10 (s, 3H), 3.42-3.48 (m, 2H), 3.75-3.81 (m, 2H), 3.84-3.97 (m, 4H), 5.27-5.31 (m, 1H), 5.34-5.38 (m, 1H), 7.41-7.45 (m, 1H), 7.77-7.82 (m, 2H), 8.20 (s, 1H). Exact mass calculated for C22H26FN3O7S 495.15, found 496.3 (MH+).

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 48 hours
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-fe3afe87ac8b41438bec75e9cc28fb4b
Source dataset
uspto-grants-2010_11
Patent number
US07838525B2

Reaction notes

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