Triethylamine → HCID 71042493, compound

HRID 1430078Notes

Reaction equation

HRID 1430078 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[NH2:16][C@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]1[OH:23].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([NH:16][C@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]2[OH:23])=[O:15])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7057408(1S,2S)-2-aminocyclohexanolHCID 71014131HCID 71014131, compound

Product 1

HCID 71042493HCID 71042493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-8-fluoroquinoline-2-carboxylic acid (C6) (1.34 g, 4.96 mmol) in dichloromethane (20 mL) was added (1S,2S)-2-aminocyclohexanol (0.857 g, 7.44 mmol), benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (2.63 g, 5.95 mmol), and triethylamine (1.04 mL, 7.44 mmol). After 17 h, the mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate (1×) and brine (1×), dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography eluting with 0-3% methanol in dichloromethane to provide 4-bromo-8-fluoro-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (C7) that gave a mass ion (ES+) of 368.8 (81Br) for M+H+.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (1×) and brine (1×)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified via silica gel chromatography
  6. washeluting with 0-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-91c104993eb743c595d5da1cbec57d2f
Source dataset
uspto-grants-2015_01
Patent number
US08940765B2

Reaction notes

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