Water → HCID 66845878, compound

HRID 1804749Notes

Reaction equation

HRID 1804749 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19](Cl)=[O:20])=[CH:5]2.C(N(CC)CC)C.Br.Br.[NH2:31][C:32]1[CH:33]=[C:34]2[CH2:40][C:39](=[O:41])[NH:38][C:35]2=[N:36][CH:37]=1.O>ClCCl>[O:41]=[C:39]1[NH:38][C:35]2=[N:36][CH:37]=[C:32]([NH:31][C:19]([C:6]3[N:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=4)[C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)=[O:20])[CH:33]=[C:34]2[CH2:40]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66846269HCID 66846269, compoundHCID 87177097HCID 87177097, compound

Product 1

HCID 66845878HCID 66845878, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.3 g (4.25 mmol) of 5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid chloride, prepared in the preceding step, 2.1 mL (14.9 mmol) of triethylamine and 1.45 (4.68 mmol) of 5-amino-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine dihydrobromide (US 2005/256 125) in 42.5 mL of dichloromethane is stirred for 24 hours at room temperature. After this time, the mixture is poured into 200 mL of water. 100 mL of dichloromethane are added and the organic phase is then separated out, washed with twice 50 mL of water and concentrated under reduced pressure. The product obtained is purified by chromatography on a column of silica, eluting with a mixture of ethyl acetate and dichloromethane. The product thus purified is taken up in 100 mL of hot methanol, and the resulting suspension is filtered. The filtrate is concentrated under reduced pressure, thus allowing 0.4 g of the expected product to be isolated.

Workup

  1. customthe organic phase is then separated out
  2. washwashed with twice 50 mL of water
  3. concentrationconcentrated under reduced pressure
  4. customThe product obtained
  5. customis purified by chromatography on a column of silica
  6. washeluting with a mixture of ethyl acetate and dichloromethane
  7. customThe product thus purified
  8. filtrationthe resulting suspension is filtered
  9. concentrationThe filtrate is concentrated under reduced pressure
  10. customto be isolated

Sources & evidence

ORD record
ord-eb954cd6ed054690b699ae00364ac100
Source dataset
uspto-grants-2013_01
Patent number
US08354425B2

Reaction notes

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