Dimethylamine → 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-N,N,5-trimethylthiazole-4-carboxamide

HRID 220382Notes

Reaction equation

HRID 220382 reaction equation
[CH:1]1([N:4]([CH:32]2[CH2:34][CH2:33]2)[C:5]([C:7]2[N:29]([CH2:30][CH3:31])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][C:22]([CH3:28])=[C:23]([C:25](O)=[O:26])[N:24]=4)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[CH3:35][NH:36][CH3:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:1]1([N:4]([CH:32]2[CH2:33][CH2:34]2)[C:5]([C:7]2[N:29]([CH2:30][CH3:31])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][C:22]([CH3:28])=[C:23]([C:25]([N:36]([CH3:37])[CH3:35])=[O:26])[N:24]=4)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581806502-(7-(Dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-5-methylthiazole-4-carboxylic acid

Product 1

HCID 581805982-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-N,N,5-trimethylthiazole-4-carboxamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-5-methylthiazole-4-carboxylic acid (43A, 30 mg, 0.063 mmol), dimethylamine, 40% aqueous (0.016 mL, 0.125 mmol) and HATU (35.7 mg, 0.094 mmol) in DMF (1 mL) was stirred at room temperature for 3 h. The solvent was evaporated off and the residue purified by silica gel chromatography (2-10% MeOH/dichloromethane). The material was further purified by preparative HPLC to give of 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-N,N,5-trimethylthiazole-4-carboxamide (20 mg, 62.5% yield) as off-white solid.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue purified by silica gel chromatography (2-10% MeOH/dichloromethane)
  3. customThe material was further purified by preparative HPLC

Sources & evidence

ORD record
ord-9f86fe2f55d042b59b8fd6fa6d3a9b17
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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