Pyridine → HCID 86614042, compound

HRID 1727170Notes

Reaction equation

HRID 1727170 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@@H:23]([C@H:24]([CH:31]([CH3:41])[CH2:32][O:33][C:34]([N:36]6[CH:40]=[CH:39][N:38]=[CH:37]6)=[O:35])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:42])[C@H:20]4[O:43][C:44](=[O:46])[CH3:45])=[O:17])[CH2:15][C@@:7]3([OH:47])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:48]1(N)[C:53](F)=[C:52](F)[C:51](F)=[C:50](N)[C:49]=1F.Cl.Cl.N1C=C[CH:65]=[CH:64][CH:63]=1>CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@@H:23]([C@@H:24]([CH:31]([CH3:41])[CH2:32][O:33][C:34]([NH:36][CH2:40][CH2:39][NH:38][C:37]6[C:53]7[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=7)[CH:65]=[CH:64][CH:63]=6)=[O:35])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:42])[C@H:20]4[O:43][C:44](=[O:46])[CH3:45])=[O:17])[CH2:15][C@@:7]3([OH:47])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 86614043HCID 86614043, compound

Product 1

HCID 86614042HCID 86614042, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To (1S,2R,4aS,5S,8R,8aR)-2-(acetyloxy)-8a-hydroxy-5-{2-[(1H-imidazol-1-ylcarbonyl)oxy]-1-methylethyl}-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Preparation 143, 80 mg, 0.12 mmol) in pyridine (5 ml) was added 4-dimethylaminopyridine (16 mg, 0.13 mmol) followed by N-1-naphthyethylenediamine dihydrochloride salt (32 mg, 0.12 mmol). After stirring the reaction mixture for 48 h, the reaction mixture was concentrated in vacuo and purified by flash chromatography eluting with hexane ethyl acetate (2:1 and then 1:1) to give the pure title compound.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography
  3. washeluting with hexane ethyl acetate (2:1

Sources & evidence

ORD record
ord-8030e92b498e431d8347eaaa4eb6bb8d
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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