Diisopropylethylamine → 2-(4,5-Dichloro-imidazol-1-yl)-N-[5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-acetamide

HRID 82123Notes

Reaction equation

HRID 82123 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:8][C:9]([OH:11])=O)[C:6]=1[Cl:7].[NH2:12][C:13]1[CH:14]=[C:15]([C:19]([C:21]2[C:29]3[CH:28]=[N:27][CH:26]=[N:25][C:24]=3[N:23]([CH:30]([CH3:32])[CH3:31])[CH:22]=2)=[O:20])[CH:16]=[N:17][CH:18]=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>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:8][C:9]([NH:12][C:13]2[CH:18]=[N:17][CH:16]=[C:15]([C:19]([C:21]3[C:29]4[CH:28]=[N:27][CH:26]=[N:25][C:24]=4[N:23]([CH:30]([CH3:32])[CH3:31])[CH:22]=3)=[O:20])[CH:14]=2)=[O:11])[C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 606695(4,5-Dichloro-1H-imidazol-1-yl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70817456(5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

Product 1

HCID 708176602-(4,5-Dichloro-imidazol-1-yl)-N-[5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-acetamideYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

(4,5-Dichloro-imidazol-1-yl)-acetic acid (25.2 mg, 0.130 mmol) was added to (5-amino-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (28.1 mg, 0.1 mmol), HATU (49.4 mg, 0.130 mmol) and DIPEA (51.7 uL, 0.300 mmol) in anhydrous DMF (1 mL). The mixture was stirred at 50° C. for 16 hours and then evaporated in vacuo and purified by prep-HPLC (method 5) to afford the title compound in 46% yield, 21.2 mg.

Workup

  1. customevaporated in vacuo
  2. custompurified by prep-HPLC (method 5)

Sources & evidence

ORD record
ord-8017ca28cd7a4aeea100dcd8dc1cc27c
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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