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Triethylamine → 1-(2-{(3R,4S)-4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-3-hydroxy-1-piperidinyl}ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one Hydrochloride

HRID 656976
Notes
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Reaction equation

HRID 656976 reaction equation
[ClH:1].Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([F:22])[CH:20]=3)[CH:15]=[CH:14][C:13]2=[O:23])[CH2:6][C@H:5]1[OH:24].C(N(CC)CC)C.[O:32]1[C:41]2[CH:40]=[C:39]([CH:42]=O)[N:38]=[CH:37][C:36]=2[O:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[ClH:1].[O:32]1[C:41]2[CH:40]=[C:39]([CH2:42][NH:3][C@H:4]3[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]4[C:21]5[C:16](=[N:17][CH:18]=[C:19]([F:22])[CH:20]=5)[CH:15]=[CH:14][C:13]4=[O:23])[CH2:6][C@H:5]3[OH:24])[N:38]=[CH:37][C:36]=2[O:35][CH2:34][CH2:33]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 674986531-{2-[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one dihydrochloride

Product 1

HCID 68993163
1-(2-{(3R,4S)-4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-3-hydroxy-1-piperidinyl}ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one Hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1-{2-[(3R,4S)-4-Amino-3-hydroxy-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one dihydrochloride (100 mg, 0.2637 mmol) was stirred in 9:1 v:v chloroform:MeOH (5 ml) at rt under argon and triethylamine (129 μl, 3.5 eq.) was added. The mixture was stirred at rt for 10 mins, then 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde (for a synthesis see WO2004058144, Example 2(c) or WO03/087098, Example 19(d)) (44 mg, 0.264 mmol) was added and the mixture was stirred at rt for 1 h before being treated with sodium triacetoxyborohydride (168 mg) added in one portion. The mixture was then stirred at rt over the weekend. Saturated aqueous sodium hydrogen cabonate (2 ml) was then added and the organic phase was diluted with DCM to bring the total volume to ca. 20 ml. The organic phase was separated using a hydrophobic frit and the aqueous phase was extracted with DCM (2×20 ml). The combined DCM extracts were evaporated under reduced pressure and purified by MDAP to give the free base of the title compound as an off-white foam (66 mg).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at rt for 1 h
  3. additionadded in one portion
  4. stirringThe mixture was then stirred at rt over the weekend
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with DCM (2×20 ml)
  7. customThe combined DCM extracts were evaporated under reduced pressure
  8. custompurified by MDAP

Sources & evidence

ORD record
ord-b3365f43d3d8493da510034b7f310726
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071592B2

Reaction notes

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