4-Methylmorpholine → (R)-2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-cyano-N-cyclopentylpropanamide

HRID 1968234Notes

Reaction equation

HRID 1968234 reaction equation
[Cl:1][C:2]1[C:3]([CH2:24][NH:25][C@H:26]([CH2:35][C:36]#[N:37])[C:27]([NH:29][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:28])=[C:4]2[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:5]2=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>C1COCC1>[Cl:1][C:2]1[C:3]2[CH2:24][N:25]([C@H:26]([CH2:35][C:36]#[N:37])[C:27]([NH:29][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)=[O:28])[C:11](=[O:13])[C:10]3=[CH:9][N:8]([S:14]([C:17]4[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[C:5]([C:4]=23)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58293505HCID 58293505, compound

Product 1

HCID 58293504(R)-2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-cyano-N-cyclopentylpropanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-5-chloro-4-((3-cyano-1-(cyclopentylamino)-1-oxopropan-2-ylamino)methyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, THF (5 mL), HATU (28.6 mg, 0.075 mmol) and 4-methylmorpholine (19.01 mg, 0.188 mmol) was stirred at room temperature for 2 h. The product was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound. [M+H] calc'd for C25H24ClN5O4S, 526; found, 526.2.

Workup

  1. customThe product was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%)
  2. customThe fractions were collected
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9a9a4909c261477a8fd290382b42ec06
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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