Sodium Hydroxide → HCID 58293505, compound

HRID 1968235Notes

Reaction equation

HRID 1968235 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][N:9]([C@H:12]([CH2:21][C:22]#[N:23])[C:13]([NH:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:14])[C:8](=[O:24])[C:7]3=[CH:25][N:26]([S:27]([C:30]4[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[C:5]([C:6]=23)=[N:4][CH:3]=1.[OH-:37].[Na+]>CO>[Cl:1][C:2]1[C:11]([CH2:10][NH:9][C@H:12]([CH2:21][C:22]#[N:23])[C:13]([NH:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:14])=[C:6]2[C:7]([C:8]([OH:24])=[O:37])=[CH:25][N:26]([S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 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

Product 1

HCID 58293505HCID 58293505, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-cyano-N-cyclopentylpropanamide in MeOH (2 mL) was added aqueous NaOH (1N, 0.5 mL). The reaction mixture was stirred for 20 min and the product was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-50%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil (0.5 mg, 2.1% from Step A starting material). 1H NMR (400 MHz, CD3OD) δ 1.37-1.72 (m, 4H) 1.83-1.95 (m, 4 H) 3.22-3.26 (m, 2 H) 3.69-3.76 (m, 1 H) 5.11 (s, 1 H) 5.14-5.17 (m, 1 H) 5.18 (s, 1 H) 7.88 (s, 1 H) 8.27 (s, 1 H). [M+H] calc'd for C18H18ClN5O2, 372; found, 372.4.

Workup

  1. customthe product was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-50%)
  2. customThe fractions were collected
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-748a5b2c0ed543b793dd6cf6b4b75e7d
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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