Diisopropylethylamine → HCID 89660235, compound

HRID 2274572Notes

Reaction equation

HRID 2274572 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][C@@H:24]([CH2:32][OH:33])[NH:23]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:12]2)=[C:6]([C:7]([N:23]2[C@H:24]([CH2:32][OH:33])[CH2:25][C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22]2)=[O:9])[CH:10]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 776757[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89649760HCID 89649760, compound

Product 1

HCID 89660235HCID 89660235, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cooled solution of 5-bromo-2-(3-(ethoxycarbonyl)-5-methyl-1H-pyrazol-1-yl)benzoic acid (45.0 g, 127.8 mmol) in DCM (450 mL) were added (S)-(1,2,3,4-tetrahydroisoquinolin-3-yl)methanol (20.8 g, 102.27 mmol), HATU (72.7 g, 191.2 mmol), DIPEA (55.7 mL, 319.6 mmol) followed by stirring at RT for 12 h. The reaction mixture was diluted with DCM (750 mL), washed with water (500 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 a liquid 50 g (79%). Rf=0.44 (55% EtOAc in hexane); 1H NMR (400 MHz, DMSO-d6): δ 8.00-7.40 (m, 3H), 7.30-7.00 (m, 4H), 6.80-6.40 (m, 1H), 5.10-3.80 (m, 7H), 3.50-2.40 (m, 3H), 2.40-2.10 (m, 3H), 1.30-1.00 (m, 3H); ES-MS: m/z 498.2 (M+H).

Workup

  1. washwashed with water (500 mL), brine (100 mL)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated invacuo
  4. customThe residue was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-a59dac3522fd4be29e07d2d17eda78bf
Source dataset
uspto-grants-2015_09
Patent number
US09126980B2

Reaction notes

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