Triethylamine → HCID 67970344, compound

HRID 82440Notes

Reaction equation

HRID 82440 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][C:3]=1[C:13]([OH:15])=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl-].[OH:44][C@@H:45]1[C@@H:50]([NH3+:51])[CH2:49][CH2:48][O:47][CH2:46]1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][C:3]=1[C:13]([NH:51][C@H:50]1[CH2:49][CH2:48][O:47][CH2:46][C@@H:45]1[OH:44])=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 584318421-Amino-4-bromo-2-naphthoic acidHCID 60209903HCID 60209903, compound

Product 1

HCID 67970344HCID 67970344, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-amino-4-bromo-2-naphthoic acid (0.644 g, 2.42 mmol) in 10 mL of acetonitrile cooled to 0° C. was added (1H-1,2,3-benzotriazol-1-yloxy)[tris(dimethylamino)]-phosphonium hexafluorophosphate (1.82 g, 4.12 mmol), O-(7-azabenzotriazol-1yl)-N,N,N,N′-tetramethyluronium hexafluorophosphate (0.921 g, 2.42 mmol), (3R,4S)-3-hydroxytetrahydro-2H-pyran-4-aminium chloride (0.310 g, 2.02 mmol), and triethylamine (0.84 mL, 6.1 mmol). The reaction was warmed to rt and stirred for 4 h. The mixture was diluted with ethyl acetate, washed with dilute aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude 1-amino-4-bromo-N-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]-2-naphthamide that gave a mass ion (ES+) of 366.9 (81Br) for [M+H]+.

Workup

  1. washwashed with dilute aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf80ec20706940fd834ac6d8d3c36960
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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