Sodium Sulfate → HCID 178478871, compound

HRID 1943220Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=4[CH:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.[O:23]=[C:24]1[CH2:29][S:28][C:27]2=[CH:30][N:31]=[C:32]([CH:34]=O)[NH:33][C:26]2=[N:25]1.C(=O)(O)[O-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:63].CO>>[ClH:63].[ClH:63].[O:23]=[C:24]1[CH2:29][S:28][C:27]2=[CH:30][N:31]=[C:32]([CH2:34][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][C@H:9]4[N:19]5[C:20]6[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=6[CH:16]=[CH:17][C:18]5=[O:21])[CH2:10]4)[CH2:6][CH2:7]3)[NH:33][C:26]2=[N:25]1

Participants

Reactant 6

HCID 24436Sodium Sulfate

HCID 516892Sodium Bicarbonate

HCID 5049666Sodium triacetoxyborohydride

HCID 21226129Dichloromethane methanol

HCID 58001796(1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione

HCID 178519956HCID 178519956, compound

Product 1

HCID 178478871HCID 178478871, compound

Procedure

A suspension of (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (for a preparation see Example 5A(j)) (0.060 g, 0.179 mmol) in 1:1 CH2Cl2/MeOH (10 mL) was treated with 7-oxo-6,7-dihydro-1H-pyrimido[5,4-b][1,4]thiazine-2-carbaldehyde (0.035 g, 0.179 mmol) and sodium bicarbonate (0.151 g, 1.793 mmol). Excess Na2SO4 was added and the reaction stirred at room temperature for 18 hours. Sodium triacetoxyborohydride (0.114 g, 0.538 mmol) was added and the reaction stirred at room temperature for 1 hour. The solution was concentrated onto silica gel and the crude material was chromatographed using a gradient of 0-100% CH2Cl2/(CH2Cl2/MeOH/NH4OH) (90:10:1). The free base of the title compound was isolated as a yellow solid (0.027 g).

Workup

stirringthe reaction stirred at room temperature for 1 hour
concentrationThe solution was concentrated onto silica gel
customthe crude material was chromatographed

Sources & evidence

ORD record: ord-471633c1e9e645218c6a04c434edbe3e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389524B2

Reaction notes

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