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Dimethylformamide → N-[5-Bromo-2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)4-methoxyphenyl]acetamide

HRID 132595
Notes
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Reaction equation

HRID 132595 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][C@H:17]([OH:32])[CH2:18][O:19][C:20]4[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=4[NH:28][C:29](=[O:31])[CH3:30])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.CN(C=O)C.B(Br)(Br)[Br:41]>C(Cl)Cl>[Br:41][C:23]1[C:24]([O:26][CH3:27])=[CH:25][C:20]([O:19][CH2:18][C@@H:17]([OH:32])[CH2:16][N:13]2[CH2:12][CH2:11][CH:10]([N:6]3[C:5]4[CH:33]=[CH:34][C:2]([F:1])=[CH:3][C:4]=4[NH:8][C:7]3=[O:9])[CH2:15][CH2:14]2)=[C:21]([NH:28][C:29](=[O:31])[CH3:30])[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 25134Boron tribromideHCID 69199245N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide

Product 1

HCID 69196349N-[5-Bromo-2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)4-methoxyphenyl]acetamideYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide (Example 32 iii)) (0.17 g, 0.36 mmol) in CH2Cl2 (5 ml) with some drops of DMF a solution of boron tribromide (BBr3) in dichloromethane (CH2Cl2) (1M, 1.08 mmol, 1.08 ml) was added dropwise under nitrogen. The stirring was continued overnight art room temperature. Then the reaction mixture was quenched with methanol, diluted with water and extracted with dichloromethane (CH2Cl2) (2×10 ml) and ethyl acetate (2×10 ml). The combined organic extracts were dried with sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography of silica gel (CH2Cl2/MeOH, 9:1) to give a colourless solid (89 mg, 0.16 mmol, 45%).

Workup

  1. additionwas added dropwise under nitrogen
  2. customart room temperature
  3. customThen the reaction mixture was quenched with methanol
  4. additiondiluted with water
  5. extractionextracted with dichloromethane (CH2Cl2) (2×10 ml) and ethyl acetate (2×10 ml)
  6. dry with materialThe combined organic extracts were dried with sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography of silica gel (CH2Cl2/MeOH, 9:1)

Sources & evidence

ORD record
ord-33f21adb4f9f4262b77f3582aafceb01
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07388020B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes