Triethylamine → 4-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide

HRID 1497321Notes

Reaction equation

HRID 1497321 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.[Cl-].[OH:16][C@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[NH3+:23].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:23][C@@H:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]2[OH:16])=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11263589[(1R,2S)-2-hydroxycyclohexyl]azanium;chlorideHCID 155308124-Bromoquinoline-2-carboxylic acid

Product 1

HCID 673239414-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the 4-bromoquinoline-2-carboxylic acid (A3) (0.10 g, 0.40 mmol) in 2.0 mL, CH2Cl2 was added (cis)-2-hydroxycyclohexanaminium chloride (0.12 g, 0.80 mmol), BOP reagent (0.35 g, 0.80 mmol), and triethylamine (0.16 mL, 1.2 mmol). The reaction mixture was stirred at room temperature for 16 h, diluted with CH2Cl2, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue subjected to silica gel chromatography eluting with 0-60% ethyl acetate in hexanes to afford 4-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide (I1) that gave a mass ion (ES+) of 349.2 (79Br) for M+H+.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-04f8c1f59127471e920f94450027aa78
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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