Triethylamine → HCID 70866057, compound

HRID 2039975Notes

Reaction equation

HRID 2039975 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:27]=[CH:26][C:12]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH3:25])=[C:20]([CH:24]=3)[C:21](O)=[O:22])=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[NH2:28][C:29]1[CH:30]=[C:31]2[CH:37]=[C:36]([C:38]([O:40][CH3:41])=[O:39])[NH:35][C:32]2=[N:33][CH:34]=1.C(N(CC)CC)C.OC1C2N=NNC=2C=CC=1.C(=O)(O)O.CN(C)CCCN=C=NCC>ClCCl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:27]=[CH:26][C:12]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH3:25])=[C:20]([CH:24]=3)[C:21]([NH:28][C:29]3[CH:30]=[C:31]4[CH:37]=[C:36]([C:38]([O:40][CH3:41])=[O:39])[NH:35][C:32]4=[N:33][CH:34]=3)=[O:22])=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 40152010Methyl 5-amino-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 68758857HCID 68758857, compoundHCID 86660457HCID 86660457, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 70866057HCID 70866057, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reactor is charged successively with 150 mg (0.4 mmol) of the solid obtained in step 3, 15 ml of anhydrous dichloromethane, 90 mg (0.4 mmol) of methyl 5-amino-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, 0.12 g (0.49 mmol) of triethylamine and 93 mg (0.61 mmol) of hydroxybenzotriazole. The mixture is stirred at room temperature for 15 min and then 90 mg (0.49 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrogen carbonate (EDCl) is added. The mixture is stirred for 16 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 6*50 ml dichloromethane. 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 (8%) of a solid is obtained.

Workup

  1. stirringThe mixture is stirred for 16 hours
  2. customThe solvent is then evaporated under reduced pressure
  3. extractionThe aqueous phase is extracted by 6*50 ml dichloromethane
  4. customdried on sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe raw product obtained
  7. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-3207b4963f9a4c15b4118f05efd57187
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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