Sodium borohydride → HCID 11547757, compound

HRID 1820683Notes

Reaction equation

HRID 1820683 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:7]([OH:8])[CH2:6][C@@H:5]([C:9]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[N:20]=3)[N:15]=[CH:14][CH:13]=2)=[O:10])[CH2:4]1.[O:24]=[C:25]1[NH:30][C:29]2[N:31]=[C:32]([CH:35]=O)[CH:33]=[CH:34][C:28]=2[S:27][CH2:26]1.[BH4-].[Na+]>C(Cl)Cl.CCO>[OH:8][C@H:7]1[C@@H:3]([CH2:2][NH:1][CH2:35][C:32]2[CH:33]=[CH:34][C:28]3[S:27][CH2:26][C:25](=[O:24])[NH:30][C:29]=3[N:31]=2)[CH2:4][C@H:5]([C:9]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[N:20]=3)[N:15]=[CH:14][CH:13]=2)=[O:10])[CH2:6]1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 57891809HCID 57891809, compound

Product 1

HCID 11547757HCID 11547757, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (±)-(1S,3R,4R)-3-(aminomethyl)-4-hydroxy-N-[6-(methyloxy)-1,5-naphthyridin-4-yl]cyclopentanecarboxamide (0.48 g, 1.51 mmole) in dry CH2Cl2 (50 mL) and dry EtOH (20 mL) at RT was added 3-oxo-3,4-dihydro-2H-pyrido[1,4]thiazine-6-carboxaldehyde (0.29 g, 1.51 mmole). After 24 h, at RT was added NaBH4 (0.063 g, 1.66 mmole). After 4 h, the reaction solution was concentrated under vacuum to a solid. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.13 g, 17%) as light yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.44 (s, 1H), 8.68 (d, J=5.1 Hz, 1H), 8.49 (d, J=5.1 Hz, 1H), 8.22 (d, J=9.0 Hz, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.16 (d, J=9.0 Hz, 1H), 6.96 (d, J=7.8 Hz, 1H), 4.12 (s, 3H), 3.92 (m, 3H), 3.49 (s, 2H), 3.38 (m, 1H), 2.95 (m, 2H), 2.39 (m, 1H), 2.50 (m, 4H), 1.91 (m, 1H). LC-MS (ES) m/e 495 (M+H)+.

Workup

  1. waitAfter 4 h
  2. concentrationthe reaction solution was concentrated under vacuum to a solid
  3. customPurification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Sources & evidence

ORD record
ord-f5c45d2583194f0681c2abd9a91cbbce
Source dataset
uspto-grants-2009_10
Patent number
US07605169B2

Reaction notes

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