Triethylamine → 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide

HRID 925623

Reaction equation

HRID 925623 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([OH:16])=O)=[CH:4][C:5]([Br:13])=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7]2.[NH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]1[OH:24].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:14]([NH:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[OH:24])=[O:16])=[CH:4][C:5]([Br:13])=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7057408(1S,2S)-2-aminocyclohexanolHCID 891885778-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

Product 1

HCID 892160708-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid (600 mg, 2.10 mmol) in DMF (7 mL) at rt was added (1S,2S)-2-aminocyclohexanol (242 mg, 2.10 mmol), BOP (1.16 g, 2.63 mmol), and Et3N (0.59 mL, 4.21 mmol). The mixture was stirred at rt for 2 h. The resulting solution was quenched with 10% aqueous NaHCO3 and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried (Na2SO4), and concentrated to afford 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide in pure form.

Workup

  1. customThe resulting solution was quenched with 10% aqueous NaHCO3
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40109f755ad14a5fb00c93bb855a2006
Source dataset
uspto-grants-2016_03
Patent number
US09284312B2

Linked notes

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