Triethylamine → HCID 69926453, compound

HRID 1183818Notes

Reaction equation

HRID 1183818 reaction equation
Cl.[NH2:2][C:3]1[C:12]([C:13]([OH:15])=O)=[CH:11][C:10]([Br:16])=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:44][C@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@@H:46]1[OH:51].C(N(CC)CC)C>ClCCl.CN(C=O)C>[NH2:2][C:3]1[C:12]([C:13]([NH:44][C@H:45]2[CH2:50][CH2:49][CH2:48][CH2:47][C@@H:46]2[OH:51])=[O:15])=[CH:11][C:10]([Br:16])=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7057408(1S,2S)-2-aminocyclohexanolHCID 67236488HCID 67236488, compound

Product 1

HCID 69926453HCID 69926453, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-amino-8-bromoisoquinoline-6-carboxylic acid hydrochloride (1.00 g, 3.29 mmol) in 10 mL of dichloromethane and 2 mL of DMF was added (1H-1,2,3-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (1.65 g, 3.74 mmol), (1S,2S)-2-aminocyclohexanol (0.430 g, 3.74 mmol), and triethylamine (1.20 mL, 8.62 mmol). After 3 h, the mixture was diluted with additional dichloromethane, washed with water, saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-3% methanol in dichloromethane, to provide crude 5-amino-8-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]isoquinoline-6-carboxamide.

Workup

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

Sources & evidence

ORD record
ord-5dd661027e994ba5992e5d80ea046820
Source dataset
uspto-grants-2014_03
Patent number
US08664387B2

Reaction notes

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