Hydrochloric Acid → HCID 178429297, compound

HRID 2235438Notes

Reaction equation

HRID 2235438 reaction equation
C[O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[C:14]4[NH:17][C:18]([NH:20][C:21](=[O:28])[C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[N:19][C:13]4=[CH:12][C:11]=3[C:10]([CH3:30])([CH3:29])[C:9]2=[O:31])=[CH:5][CH:4]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[C:14]4[NH:17][C:18]([NH:20][C:21](=[O:28])[C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[N:19][C:13]4=[CH:12][C:11]=3[C:10]([CH3:29])([CH3:30])[C:9]2=[O:31])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 178490845HCID 178490845, compound

Product 1

HCID 178429297HCID 178429297, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[5-(4-Methoxy-benzyl)-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-benzamide (10 mg; 0.02 mmol) is suspended in a BBr3 solution in CH2Cl2 (1 M; 100 μl) and stirred at RT for 18 h. After addition of hydrochloric acid (200 μl; 1 N) the mixture is stirred at RT for another 1 h and then evaporated to dryness. The crude material is purified by preparative RP-HPLC, eluted with MeCN/water to yield the desired compound (5 mg).

Workup

  1. stirringis stirred at RT for another 1 h
  2. customevaporated to dryness
  3. customThe crude material is purified by preparative RP-HPLC
  4. washeluted with MeCN/water

Sources & evidence

ORD record
ord-151933d5f9654402b99bb85199ae5a27
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…