Dichloromethane → HCID 68796684, compound

HRID 2039978Notes

Reaction equation

HRID 2039978 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:26])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9])=O.ClCCl.[NH2:30][C:31]1[CH:32]=[C:33]2[CH:39]=[C:38]([C:40]([O:42][CH3:43])=[O:41])[NH:37][C:34]2=[N:35][CH:36]=1.C(O[BH3-])(=O)C.[Na+]>C(O)(=O)C>[CH3:25][N:22]1[CH2:21][CH2:20][N:19]([CH2:18][C:15]2[CH:14]=[CH:13][C:12]([C:11]([NH:10][C:5]3[CH:6]=[CH:7][C:8]([CH3:9])=[C:3]([CH:4]=3)[CH2:1][NH:30][C:31]3[CH:32]=[C:33]4[CH:39]=[C:38]([C:40]([O:42][CH3:43])=[O:41])[NH:37][C:34]4=[N:35][CH:36]=3)=[O:26])=[CH:17][CH:16]=2)[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 23670382SodiumacetoxyborohydrideHCID 40152010Methyl 5-amino-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 87562064HCID 87562064, compound

Product 1

HCID 68796684HCID 68796684, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reactor is charged with 120 mg (0.34 mmol) of the solid obtained in step 2, 15 ml of anhydrous dichloromethane, 78 mg (0.41 mmol) of methyl 5-amino-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, 216 mg (1.02 mmol) of sodium acetoxyborohydride and a catalytic amount of acetic acid. The mixture is stirred at room temperature for 24 hours. The solvent is then evaporated under reduced pressure and the residue is taken off in 100 ml of water. The aqueous phase is extracted by 3*30 ml ethyl acetate. The aqueous phases are combined, dried on sodium sulphate and then evaporated under reduced pressure. The raw product obtained is purified by preparative HPLC and 18 mg of a solid is obtained (10%).

Workup

  1. customThe solvent is then evaporated under reduced pressure
  2. extractionThe aqueous phase is extracted by 3*30 ml ethyl acetate
  3. customdried on sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe raw product obtained
  6. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-3c752877b3e74669990baba8a9b886c4
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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