Triethylamine → 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)-N-hydroxyhexanamide

HRID 20704Notes

Reaction equation

HRID 20704 reaction equation
CN(C([O:8][N:9]1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30]([Cl:55])[C:31]=1[NH:32][C:33]1[C:42]2[C:37](=[C:38]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][C:51]([OH:53])=O)[C:39]([O:43][CH3:44])=[CH:40][CH:41]=2)[O:36][C:35](=[O:54])[CH:34]=1.C(N(CC)CC)C.NO.Cl>CS(C)=O>[Cl:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30]([Cl:55])[C:31]=1[NH:32][C:33]1[C:42]2[C:37](=[C:38]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][C:51]([NH:9][OH:8])=[O:53])[C:39]([O:43][CH3:44])=[CH:40][CH:41]=2)[O:36][C:35](=[O:54])[CH:34]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 248497096-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoic acid

Product 1

HCID 248492946-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)-N-hydroxyhexanamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

HATU (25 mg, 0.066 mmol) was added to a solution of 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoic acid (25 mg, 0.053 mmol, Example 44), triethylamine (0.05 mL, 0.36 mmol), and DMSO (0.5 mL). After 5 min, NH2OH•HCl (10 mg, 0.14 mmol) was added. After an additional 17 h, the mixture was diluted with DMSO (1 mL), filtered through cotton, and the filtrate purified by reverse-phase HPLC (1:9→3:2; acetonitrile:water) to give 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)-N-hydroxyhexanamide: 1H NMR (400 MHz, DMSO-d6): δ 10.32 (s, 1H), 9.51 (s, 1H), 8.81 (s, 2H), 7.94 (d, 1H), 7.20 (d, 1H), 4.63 (s, 1H), 3.96 (t, 2H), 3.92 (s, 3H), 1.96 (t, 2H), 1.67 (m, 2H), 1.54 (m, 2H), 1.43 (m, 2H); MS (ESI): 481.9.

Workup

  1. waitAfter an additional 17 h
  2. filtrationfiltered through cotton
  3. customthe filtrate purified by reverse-phase HPLC (1:9→3:2; acetonitrile:water)

Sources & evidence

ORD record
ord-7edf5152d6a248e487dfbfe9620834c6
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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