Pyridine → HCID 67995106, compound

HRID 2042958Notes

Reaction equation

HRID 2042958 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)=[CH:23][N:24]=1.CCN=C=NCCCN(C)C.N1C=CC=CC=1.[CH3:47][O:48][C:49]1[CH:50]=[C:51]([CH:55]=[CH:56][C:57]=1[O:58][CH3:59])[C:52](O)=[O:53]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:47][O:48][C:49]1[CH:50]=[C:51]([CH:55]=[CH:56][C:57]=1[O:58][CH3:59])[C:52]([O:18][CH2:17][C@@H:10]1[C@@H:11]([OH:16])[C@H:12]([OH:15])[C@@H:13]([OH:14])[C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:29]=[CH:28][S:27][CH:26]=4)=[CH:23][N:24]=3)[CH:4]=2)[O:9]1)=[O:53]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7121Veratric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 51346777HCID 51346777, compound

Product 1

HCID 67995106HCID 67995106, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 48 (150 mg, 0.33 mmol), EDCI (130 mg, 0.66 mmol) and DMAP (20 mg, 0.16 mmol) and pyridine (0.13 ml, 1.65 mmol) in CH2Cl2 (4 ml) was added 3,4-dimethoxybenzoic acid (120 mg, 0.66 mmol) at room temperature and stirred for 16 hours. The reaction mixture was diluted with CH2Cl2 (8 ml), and washed with brine (8 ml). The organic phase was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by prep HPLC (C18) to provide the titled compound (55 mg, 27%).

Workup

  1. washwashed with brine (8 ml)
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-3d8554c0820f4dd59b36c2518e85afd1
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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