Hydrochloric Acid → HCID 11949831, compound

HRID 221963Notes

Reaction equation

HRID 221963 reaction equation
N1C=CC=CC=1.Cl.[NH2:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[C:15]2=[O:34])=[CH:11][CH:10]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>O.C1COCC1>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:16]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:14]([CH2:13][C:12]3[CH:11]=[CH:10][C:9]([NH:8][S:38]([CH3:37])(=[O:40])=[O:39])=[CH:36][CH:35]=3)[C:15]2=[O:34])=[CH:29][CH:28]=1)([CH3:31])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59707066HCID 59707066, compound

Product 1

HCID 11949831HCID 11949831, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (0.3 mL, 3.72 mmol) was added to a suspension of the hydrochloride of 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-1,3-dihydrobenzimidazol-2-one (Q) (717 mg, 1.7 mmol) in abs. THF (20 mL). The reaction mixture was stirred at RT for 10 min, methanesulphonyl chloride (0.13 mL, 1.7 mmol, dissolved in abs. THF (1 mL)) was added within a period of 5 min, and the reaction mixture was again stirred at RT over a period of 17 h. To the reaction mixture there was then added H2O (10 mL) followed, after 10 min, by H2O (100 mL). After an hour the precipitated solid matter was separated through a frit and then dried in vacuo. The desired product N-{4-[3-(4-tert-Butyl-benzyl)-2-oxo-2,3-dihydrobenzoimidazol-1-ylmethyl]phenyl}methanesulfonamide (60) was obtained in a yield of 680 mg (86% of theory, mp: 228-230° C.).

Workup

  1. stirringthe reaction mixture was again stirred at RT over a period of 17 h
  2. customAfter an hour the precipitated solid matter was separated through a frit
  3. customdried in vacuo

Sources & evidence

ORD record
ord-21e362902db247269fbc7fc7f34ff2f0
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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