Water → HCID 54575522, compound

HRID 1519245Notes

Reaction equation

HRID 1519245 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][OH:22])=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[C:34]1[CH:44]=[CH:43][C:37]([C:38]([NH:40][CH2:41][CH3:42])=[O:39])=[CH:36][N:35]=1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][O:22][C:34]2[N:35]=[CH:36][C:37]([C:38]([NH:40][CH2:41][CH3:42])=[O:39])=[CH:43][CH:44]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 299194256-Bromo-N-ethylpyridine-3-carboxamideHCID 71184222HCID 71184222, compound2×

Product 1

HCID 54575522HCID 54575522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol (intermediate B1.1, 0.03 g, 0.09 mmol) in 0.6 ml of THF was added 1M NaHMDS in THF (0.11 ml, 0.11 mmol). After 10 min at rt, 6-bromo-N-ethylnicotinamide (0.02 g, 0.08 mmol) was added. After 3 h, a drop of water was added to the reaction and purified by reverse phase HPLC to give 6-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)-N-ethylpyridine-3-carboxamide. 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=2.4 Hz, 1H), 8.35 (d, J=2.4 Hz, 1H), 8.08 (m, 2H), 7.96 (dd, J=8.6, 2.6 Hz, 1H), 7.48 (dd, J=8.4, 2.6 Hz, 1H), 7.13 (m, 2H), 6.96 (d, J=8.4 Hz, 1H), 6.8 (d, J=8.8 Hz, 1H), 5.94 (s, 1H), 5.48 (s, 2H), 3.46 (m, 2H), 1.24 (t, J=7.3 Hz, 3H); HRMS exact mass calc for C23H18ClFN4O3S [M+H]+: 485.0845; observed: 485.0854.

Workup

  1. waitAfter 3 h
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d4483f0126964b69b6d2f739d337c22e
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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