Sodium hydride → HCID 72699522, compound

HRID 715767Notes

Reaction equation

HRID 715767 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]3[CH:19]=[CH:20][N:21]=[C:15]3[CH:14]=2)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[C:24]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:25]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1>O1CCCC1>[N:21]1[CH:20]=[CH:19][N:16]2[CH:17]=[CH:18][C:13]([CH2:12][NH:11][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:30]([C:25]4[C:24]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:32])=[O:31])=[CH:3][CH:4]=3)=[O:10])=[CH:14][C:15]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27566802-Phenylbenzene-1-sulfonyl chlorideHCID 86701940HCID 86701940, compound

Product 1

HCID 72699522HCID 72699522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 4 mL vial was mixed 1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea (50 mg, 0.178 mmol) in anhydrous tetrahydrofuran (2 mL). To this mixture at room temperature was added 60% sodium hydride (24.88 mg, 0.622 mmol). The reaction was stirred about 30 minutes and biphenyl-2-sulfonyl chloride (53.9 mg, 0.213 mmol) was added. The reaction mixture stirred overnight at room temperature and was quenched with saturated ammonium chloride and water. The aqueous solution was extracted with dichloromethane and 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 9.74 (bs, 1H), 8.56 (s, 1H), 8.47 (dd, J=6.9, 0.9 Hz, 1H), 7.95 (dd, J=7.8, 1.4 Hz, 1H), 7.87 (dd, J=1.2, 0.6 Hz, 1H), 7.62 (m, 1H), 7.54 (m, 1H), 7.51 (m, 1H), 7.38 (m, 4H), 7.30-7.20 (m, 5H), 6.82 (m, 3H), 6.66 (t, J=6.0 Hz, 1H), 4.30 (d, J=6.0 Hz, 2H); (ESI(+)) m/e 498 (M+H)+.

Workup

  1. stirringThe reaction mixture stirred overnight at room temperature
  2. customwas quenched with saturated ammonium chloride and water
  3. extractionThe aqueous solution was extracted with dichloromethane and 10% methanol/dichloromethane
  4. concentrationconcentrated
  5. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-406c6f70035340c593c1419097c4ccc1
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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