Sodium hydride → HCID 86701965, compound

HRID 715789Notes

Reaction equation

HRID 715789 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH:15]1[CH2:18][CH:17]([C:19]2[CH:37]=[CH:36][C:22]([C:23]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][N:30]4[CH:33]=[CH:34][N:35]=[C:29]4[CH:28]=3)=[O:24])=[CH:21][CH:20]=2)[CH2:16]1.[H-].[Na+].[CH3:40][CH:41]([S:43](Cl)(=[O:45])=[O:44])[CH3:42]>O1CCCC1>[N:35]1[CH:34]=[CH:33][N:30]2[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:23](=[O:24])[C:22]3[CH:21]=[CH:20][C:19]([CH:17]4[CH2:18][N:15]([S:43]([CH:41]([CH3:42])[CH3:40])(=[O:45])=[O:44])[CH2:16]4)=[CH:37][CH:36]=3)=[CH:28][C:29]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 824082-Propanesulfonyl chlorideHCID 86701966HCID 86701966, compound

Product 1

HCID 86701965HCID 86701965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 4 mL vial was mixed 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide bis(2,2,2-trifluoroacetate) (60 mg, 0.112 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature. To this mixture was added in portions 60% sodium hydride in mineral oil (22.45 mg, 0.561 mmol). This heterogeneous mixture was stirred 1 hour. To this was added propane-2-sulfonyl chloride (0.015 mL, 0.135 mmol) at and reaction mixture was stirred for 3 hours. The mixture was quenched with water, and product was extracted with 10% methanol/dichloromethane. The organic layers were combined, concentrated and purified by normal phase chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (m, 1H), 8.47 (d, J=7.0 Hz, 1H), 7.90 (m, 3H), 7.48 (m, 3H), 7.37 (s, 1H), 6.84 (m, 1H), 4.50 (d, J=5.9 Hz, 2H), 4.22 (m, 2H), 3.93 (m, 3H), 3.48 (m, 1H), 1.25 (d, J=5.9 Hz, 6H); MS (ESI(+)) m/e 413 (M+H)+.

Workup

  1. customreaction mixture
  2. stirringwas stirred for 3 hours
  3. customThe mixture was quenched with water, and product
  4. extractionwas extracted with 10% methanol/dichloromethane
  5. concentrationconcentrated
  6. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-fd873e3b91ca45f8b35315ca0100d974
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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