2,4,6-Trimethylpyridine → HCID 56605553, compound

HRID 987219Notes

Reaction equation

HRID 987219 reaction equation
[O:1]=[C:2]1[N:11]2[C:6]([CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:10]2)=[CH:5][C:4]([C:23]([OH:25])=O)=[CH:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.C([O:55][C:56](=[O:70])[C@@H:57]([NH:60][S:61]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)(=[O:63])=[O:62])[CH2:58][NH2:59])(C)(C)C.N1C(C)=CC(C)=CC=1C>>[C:64]1([S:61]([NH:60][C@@H:57]([CH2:58][NH:59][C:23]([C:4]2[CH:5]=[C:6]3[N:11]([C:2](=[O:1])[CH:3]=2)[CH:10]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:22]=2)[CH:8]=[CH:7]3)=[O:25])[C:56]([OH:70])=[O:55])(=[O:62])=[O:63])[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1

Participants

5

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochlorideHCID 22988038HCID 22988038, compound

Product 1

HCID 56605553HCID 56605553, compoundYield 90.9%

Procedure

To a mixture of 4-oxo-7-[3-(pyrimidin-2-ylamino)-propoxy]-4H-quinolizine-2-carboxylic acid (6.9 mg, 0.020 mmol), was added HATU (9.9 mg, 0.026 mmol), (S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride (8.1 mg, 0.024 mmol) and collidine (19 μl, 0.140 mmol). The mixture was stirred for 45 minutes, concentrated and flash chromatographed (0-5% methanol in dichiloromethane) to give 10.3 mg (82% yield) of desired product.

Workup

  1. concentrationconcentrated
  2. customflash chromatographed (0-5% methanol in dichiloromethane)

Sources & evidence

ORD record
ord-0a933d8671b44343ba6b349bac695f97
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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