HCID 13895871, compound → HCID 86748031, compound

HRID 1729538Notes

Reaction equation

HRID 1729538 reaction equation
[Cl:1][CH2:2][C@@H:3]1[CH2:7][N:6]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15](NC(C2NC4C(C=2)=CC=CC=4)=O)=[CH:14][CH:13]=3)=[O:9])[C:5]2[CH:31]=[C:32]([OH:39])[C:33]3[NH:34][CH:35]=[C:36]([CH3:38])[C:37]=3[C:4]1=2>N1C=CC=CC=1>[C:32]([O:39][C:32]1[C:33]2[NH:34][CH:35]=[C:36]([CH3:38])[C:37]=2[C:4]2[CH:3]([CH2:2][Cl:1])[CH2:7][N:6]([C:8]([C:10]3[NH:11][C:12]4[C:17]([CH:18]=3)=[CH:16][C:15]([N:11]3[C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[CH:18]=[C:10]3[C:8]([NH2:6])=[O:9])=[CH:14][CH:13]=4)=[O:9])[C:5]=2[CH:31]=1)(=[O:39])[CH3:31]

Participants

3

Reactant 1

HCID 13895871HCID 13895871, compound

Product 1

HCID 86748031HCID 86748031, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

15 mg (0.028 mmol) of (S)-N-[2-[[1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-1H-Indole-2-carboxamide is dissolved in 2 ml of dry pyridine at 5° C., degassed with nitrogen and treated with 0.005 ml of acetyl chloride. After 30 min. at 5° C., the solution is warmed to room temperature, quenched with 1 ml of water, diluted with 50 ml of ethyl acetate, and washed with two 20 ml portions of 1:1 brine/1N hydrochloric acid, and then brine. The solution is dried with sodium sulfate, filtered, adsorbed on 1 g of Celite™, and flash chromatographed on 10 g of silica gel, eluting with 50% ethyl acetate in hexane to give in fractions (25 ml) 6-12 the title compound as a solid.

Workup

  1. customdegassed with nitrogen
  2. additiontreated with 0.005 ml of acetyl chloride
  3. customquenched with 1 ml of water
  4. additiondiluted with 50 ml of ethyl acetate
  5. washwashed with two 20 ml portions of 1:1 brine/1N hydrochloric acid
  6. dry with materialThe solution is dried with sodium sulfate
  7. filtrationfiltered
  8. customchromatographed on 10 g of silica gel
  9. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d21123153f1749799941f3d13dfb493a
Source dataset
uspto-grants-1994_07
Patent number
US05332837

Reaction notes

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