Dibutylamine → HCID 89660113, compound

HRID 2274566Notes

Reaction equation

HRID 2274566 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]1[C:13]([C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]1[C:28]([CH3:29])=[CH:27][C:26]([C:30](O)=[O:31])=[N:25]1)=[O:14].[CH2:33]([NH:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH3:36].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH2:33]([N:37]([CH2:38][CH2:39][CH2:40][CH3:41])[C:30]([C:26]1[CH:27]=[C:28]([CH3:29])[N:24]([C:16]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=2[C:13]([N:4]2[C@H:3]([CH2:2][OH:1])[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5]2)=[O:14])[N:25]=1)=[O:31])[CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 8148DibutylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89660118HCID 89660118, compound

Product 1

HCID 89660113HCID 89660113, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (5)-1-(2-(3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-nitrophenyl)-5-methyl-1H-pyrazole-3-carboxylic acid (14.0 g, 32.1 mmol) in DMF (150 mL) were added dibutylamine (8.6 mL, 48.2 mmol), EDC.HCl (9.2 g, 48.2 mmol), HOBT (5.63 g, 41.7 mmol) followed by stirring at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc (300 mL×2) twice. The combined organic layers were washed with water (300 mL), brine (100 mL), dried over sodium sulphate and concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford the title compound as and ‘off white’ solid 9 g (51%). Rf=0.47 (25% EtOAc in hexane); 1H NMR (400 MHz, DMSO-d6): δ 8.62-8.22 (m, 2H), 8.00-7.80 (m, 1H), 7.30-6.84 (m, 4H), 6.60-6.35 (m, 1H), 5.20-3.80 (m, 3H), 3.79-2.40 (m, 9H), 2.38-2.20 (m, 3H), 1.60-0.50 (m, 14H); LC-MS: m/z 548.0 (M+H).

Workup

  1. extractionextracted with EtOAc (300 mL×2) twice
  2. washThe combined organic layers were washed with water (300 mL), brine (100 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated invacuo
  5. customThe residue was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-6a64e2f3806e409a9a2e183b53fb2fd2
Source dataset
uspto-grants-2015_09
Patent number
US09126980B2

Reaction notes

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