Diisopropylethylamine → HCID 59314194, compound

HRID 1047737Notes

Reaction equation

HRID 1047737 reaction equation
N1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH2:4][CH2:3][CH2:2]1.[CH2:14]([O:16][C:17]([C:19]1([NH2:29])[CH2:27][C:26]2[CH:25]=[N:24][C:23]([CH3:28])=[CH:22][C:21]=2[CH2:20]1)=[O:18])[CH3:15].[CH3:30]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:14]([O:16][C:17]([C:19]1([NH:29][C:11]([C:9]2[C:10]3[CH2:30][CH2:2][CH2:3][CH2:4][C:5]=3[CH:6]=[CH:7][CH:8]=2)=[O:13])[CH2:27][C:26]2[CH:25]=[N:24][C:23]([CH3:28])=[CH:22][C:21]=2[CH2:20]1)=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27855891,2,3,4-Tetrahydroquinoline-8-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59314162HCID 59314162, compound

Product 1

HCID 59314194HCID 59314194, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (240 mg, 1.36 mmol), 6-amino-3-methyl-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester (not pure, 300 mg, 1.36 mmol), HATU (608 mg, 1.60 mmol) in anhydrous DMF (10 mL) is added DIPEA (264 μL, 1.60 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (40 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by HPLC to give a product (82) as a colorless oil (100 mg, 19%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (40 mL)
  3. washwashed with water (1×10 mL) and brine (2×10 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-c23b017c63634c2da2109cf128f094c4
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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