3,6-Dichloropyridazine → HCID 86585869, compound

HRID 1977040Notes

Reaction equation

HRID 1977040 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([CH2:18][OH:19])[CH2:16][CH2:17][C@H:10]2[CH2:9]1)(OC(C)(C)C)=O.[F:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[C:25]([F:27])[CH:26]=1.[Cl:29][C:30]1[N:31]=[N:32]C(Cl)=[CH:34][CH:35]=1>>[F:20][C:21]1[CH:22]=[C:23]([CH:24]=[C:25]([F:27])[CH:26]=1)[O:19][CH2:18][C@H:15]1[CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:1]3[N:32]=[N:31][C:30]([Cl:29])=[CH:35][CH:34]=3)[CH2:9][C@@H:10]2[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 673313,6-DichloropyridazineHCID 759283,5-DifluorophenolHCID 22882696HCID 22882696, compound

Product 1

HCID 86585869HCID 86585869, compound

Procedure

A mixture of (7R,9aS)-N-BOC-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (WO 93/25552) and 3,5-difluorophenol were coupled followed by N-BOC deprotection according to Preparation 9. The product from this reaction was coupled with 3,6-dichloropyridazine according to Preparation 3 to give the title compound. mp (—HCl) 254-259° C. 13C NMR (base, CDCl3): δ26.7, 28.9, 36.1, 45.1, 50.4, 54.3, 58.4, 60.3, 71.4, 96.3, 95.0, 98.4, 115.2, 128.8, 146.8, 158.8.

Workup

  1. customaccording to Preparation 9

Sources & evidence

ORD record
ord-7c732d84fa4a439aa6200201a3de7aa5
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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