Triethylamine → HCID 67386992, compound

HRID 908321Notes

Reaction equation

HRID 908321 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[C:23](=[O:24])[CH2:22][CH:21]([C:25]([O:27]C)=[O:26])[CH2:20]3)=[CH:15][CH:14]=2)=[C:7]2[C:12]=1[CH:11]=[N:10][CH:9]=[CH:8]2.[OH-].[Na+].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:13]2[CH:14]=[CH:15][C:16]([N:19]3[C:23](=[O:24])[CH2:22][CH:21]([C:25]([OH:27])=[O:26])[CH2:20]3)=[CH:17][CH:18]=2)=[C:7]2[C:12]=1[CH:11]=[N:10][CH:9]=[CH:8]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58828844HCID 58828844, compound

Product 1

HCID 67386992HCID 67386992, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 1-(4-(8-methoxyisoquinolin-5-yl)phenyl)-5-oxopyrrolidine-3-carboxylate (220 mg, 0.58 mmol) in dioxane (2 mL) was treated with NaOH (1N, 1 mL). The mixture was heated to 80° C. for 17 h and the solvents were evaporated to dryness. MS (ESI pos. ion) m/z: 363 (M+H). The acid was dissolved in DMF (2 mL) and was treated with HBTU (450 mg, 1.25 mmol) and Et3N (1 mL). The solution was divided into two equal portions and was used directly.

Workup

  1. customthe solvents were evaporated to dryness
  2. dissolutionThe acid was dissolved in DMF (2 mL)

Sources & evidence

ORD record
ord-991abe7f7c2a4acdaad03154b2d636fb
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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