Triethylamine → HCID 53261779, compound

HRID 60113Notes

Reaction equation

HRID 60113 reaction equation
[F:1][C:2]1[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:20][CH:19]=[C:18]([F:29])[C:3]=1[C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15](O)=[O:16])[CH:13]=2)[NH:8][CH:7]=1)=[O:5].F[P-](F)(F)(F)(F)F.[N:37]1(OC(N(C)C)=[N+](C)C)[C:41]2[CH:42]=[CH:43][CH:44]=C[C:40]=2[N:39]=N1.C(N(CC)CC)C.N1C=CC=C(N)C=1>CN(C)C=O.O.C(OCC)(=O)C>[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([NH:37][C:15]([C:12]2[CH:13]=[C:14]3[C:6]([C:4](=[O:5])[C:3]4[C:18]([F:29])=[CH:19][CH:20]=[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[C:2]=4[F:1])=[CH:7][NH:8][C:9]3=[N:10][CH:11]=2)=[O:16])[CH:40]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58087848HCID 58087848, compound

Product 1

HCID 53261779HCID 53261779, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a reaction vial, 3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (41, 13 mg, 0.031 mmol) is dissolved in 0.5 mL of N,N-dimethylformamide and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (17 mg, 0.046 mmol) is added followed by triethylamine (21 μL, 0.15 mmol). The mixture is stirred for 15 minutes, then pyridin-3-ylamine (42, 29 mg, 0.31 mmol) is added and the reaction is stirred at room temperature overnight. The reaction is diluted with water and ethyl acetate. The aqueous phase is separated and extracted with ethyl acetate. The organic layers are combined and dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by reverse phase chromatography to provide the desired compound. MS (ESI) [M+H+]+=500.0.

Workup

  1. stirringthe reaction is stirred at room temperature overnight
  2. customThe aqueous phase is separated
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material is purified by reverse phase chromatography

Sources & evidence

ORD record
ord-1618c89959ef4f9fb4f467d868ea7a5d
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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