Benzylamine → HCID 178522815, compound

HRID 456636Notes

Reaction equation

HRID 456636 reaction equation
C(O[C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[NH:8][CH:7]=1)=[O:5])C.Cl.CN(C)CCCN=C=NCC.[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:32]([NH:39][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[NH:8][CH:7]=1)=[O:5])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178469891HCID 178469891, compound

Product 1

HCID 178522815HCID 178522815, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (50 mg, 0.22 mmol) (from example 11), p-hydroxybenzotriazole hydrate (HOBt) (74 mg, 2.5 eq.), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDAC HCl) (105 mg, 2.5 eq.), benzylamine (94 mg, 4 eq.) and triethylamine (TEA) (0.5 mL) in DMF (1 mL) was heated at 40° C. for overnight. The reaction was concentrated and the residue was purified on a silica gel column to give 40 mg of the titled compound as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-40c9fa4130e541b08455a87cc4b370d3
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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