Sodium borohydride → N-(4-{2-[7-(2-Hydroxy-ethyl)-[1,8]naphthyridin-4-ylamino]-4-methyl-phenylsulfanyl}-phenyl)-acetamide

HRID 883884Notes

Reaction equation

HRID 883884 reaction equation
C([O:3][C:4](=O)[CH:5]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][C:17]=2[NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=2[S:29][C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=2)[N:12]=1)C(OCC)=O)C.[BH4-].[Na+]>CCO>[OH:3][CH2:4][CH2:5][C:11]1[N:12]=[C:13]2[C:18]([C:17]([NH:21][C:22]3[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=3[S:29][C:30]3[CH:31]=[CH:32][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:34][CH:35]=3)=[CH:16][CH:15]=[N:14]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 672508532-{5-[2-(4-Acetylamino-phenylsulfanyl)-5-methyl-phenylamino]-[1,8]naphthyridin-2-yl}-malonic acid diethyl ester

Product 1

HCID 24898183N-(4-{2-[7-(2-Hydroxy-ethyl)-[1,8]naphthyridin-4-ylamino]-4-methyl-phenylsulfanyl}-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 23b (56 mg, 0.10 mmol) was reacted with NaBH4 (40 mg, 1.00 mmol) in 5 mL EtOH for 24 h. Quenched with aqueous NH4Cl and adjusted to pH 7 with dilute HCl. Extracted with EtOAc and dried over Na2SO4, filtered and concentrated under vacuum giving the crude title compound which was purified by HPLC with TFA giving the trifluoroacetic acid salt (15 mg, 25%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.04 (s, 3 H) 2.35 (s, 3 H) 3.16 (t, J=6.43 Hz, 2 H) 3.91 (t, J=6.25 Hz, 2 H) 6.31 (d, J=6.99 Hz, 1 H) 7.14 (d, J=8.09 Hz, 1 H) 7.22-7.33 (m, 4 H) 7.51 (d, J=8.82 Hz, 2 H) 7.83 (d, J=8.82 Hz, 1 H) 8.42 (d, J=6.99 Hz, 1 H) 8.94-9.05 (m, 1 H) 10.04 (s, 1 H) 11.03 (s, 1 H) 14.40 (s, 1 H); MS (ESI+) m/z 445 (M+H−TFA)+.

Workup

  1. customQuenched with aqueous NH4Cl
  2. extractionExtracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fc2e52da10d74dd8aa842e0ac5751294
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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