Hydrochloric Acid → HCID 178425297, compound

HRID 2235477Notes

Reaction equation

HRID 2235477 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[C:13]4[NH:16][C:17]([NH:19][C:20](=[O:28])[C:21]5[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=5)=[N:18][C:12]4=[CH:11][C:10]=3[C:9]([CH3:30])([CH3:29])[C:8]2=[O:31])=[C:4]([O:34]C)[CH:3]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[C:13]4[NH:16][C:17]([NH:19][C:20](=[O:28])[C:21]5[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=5)=[N:18][C:12]4=[CH:11][C:10]=3[C:9]([CH3:29])([CH3:30])[C:8]2=[O:31])=[C:4]([OH:34])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 178492926HCID 178492926, compound

Product 1

HCID 178425297HCID 178425297, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[5-(4-Fluoro-2-methoxy-benzyl)-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-3-methyl-benzamide (5 mg) is suspended in a BBr3 solution in CH2Cl2 (1 M; 33 μl) and stirred at RT for 10 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 (3.2 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-09d94dbdbbb945de8416df7bb8b91183
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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