Cyclopropylamine → HCID 58180560, compound

HRID 220365Notes

Reaction equation

HRID 220365 reaction equation
[CH:1]1([N:4]([CH:31]2[CH2:33][CH2:32]2)[C:5]([C:7]2[N:28]([CH2:29][CH3:30])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][C:22]([C:25](O)=[O:26])=[CH:23][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.[CH:34]1([NH2:37])[CH2:36][CH2:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:34]1([NH:37][C:25]([C:22]2[S:21][C:20]([NH:19][C:12]3[N:11]=[C:10]4[N:28]([CH2:29][CH3:30])[C:7]([C:5](=[O:6])[N:4]([CH:1]5[CH2:3][CH2:2]5)[CH:31]5[CH2:32][CH2:33]5)=[CH:8][C:9]4=[C:14]4[N:15]([CH3:18])[CH:16]=[N:17][C:13]=34)=[N:24][CH:23]=2)=[O:26])[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58180599HCID 58180599, compound

Product 1

HCID 58180560HCID 58180560, compoundYield 19.82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)thiazole-5-carboxylic acid (example 20A, 13.97 mg, 0.030 mmol) in DMF (300 μL) was added cyclopropylamine (4.16 μL, 0.060 mmol), HATU (14.83 mg, 0.039 mmol), and Hünig's Base (15.72 μL, 0.090 mmol). The reaction mixture was stirred at rt 1 h and concentrated in vacuo: The residue was taken up in MeOH and purified by preparative HPLC. N-Cyclopropyl-2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)thiazole-5-carboxamide (3 mg, 19.82% yield) was isolated as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-e4693502107b4076b1c74d0cf44a1e0d
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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