Ethylamine → HCID 45378149, compound

HRID 1627229Notes

Reaction equation

HRID 1627229 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[C:15]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21]([C:26]([OH:28])=O)=[CH:20]4)[CH:14]=[CH:13][N:12]=2)=[O:10])=[CH:3][CH:2]=1.CN(C(O[N:37]1N=N[C:39]2C=CC=N[C:38]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C(N)C>CN(C)C=O.C(OCC)(=O)C>[CH2:38]([NH:37][C:26]([C:21]1[NH:22][C:23]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:9](=[O:10])[NH:8][CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH:16]=1)=[CH:25][CH:24]=2)=[O:28])[CH3:39]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45377841HCID 45377841, compound

Product 1

HCID 45378149HCID 45378149, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-{2-[(Pyridin-4-ylmethyl)-carbamoyl]-pyridin-4-yl}-1H-indole-2-carboxylic acid (40 mg, 0.1 mmol) in N,N dimethylformamide (1 ml) is added HATU (49 mg, 0.13 mmol) followed by N,N-diisopropylethylamine (0.025 ml. 0.12 mmol). The reaction is stirred for ½ hour. The ethylamine (64 uL, 0.13 mmol) is added and the reaction mixture stirred for 24 hours. The reaction mixture is diluted with ethyl acetate and is washed 3× with water, 1× with sodium carbonate and 1× with brine. The organic layer dried over Na2SO4, filtered, and is evaporated in vacuo. The crude product is purified by reverse phase HPLC to give the title compound 8 mg, 19%, LC/MS ESI m/z (M+H)+=400.4.

Workup

  1. stirringthe reaction mixture stirred for 24 hours
  2. washis washed 3× with water, 1× with sodium carbonate and 1× with brine
  3. dry with materialThe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. customis evaporated in vacuo
  6. customThe crude product is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f379f5f12d194549afa4f4b1c236ae23
Source dataset
uspto-grants-2014_07
Patent number
US08785489B2

Reaction notes

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