Diisopropylethylamine → HCID 67497569, compound

HRID 1628269Notes

Reaction equation

HRID 1628269 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:7]=1)=[O:4].S1[CH:29]=[C:28]([CH:30]=[O:31])N=C1.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:33].[Na+].[CH3:46][CH2:47]N(C(C)C)C(C)C>ClCCCl>[C:19]1([CH2:18][C@H:2]([NH:1][CH2:32][CH2:33][CH:29]2[CH2:47][CH2:46][O:31][CH2:30][CH2:28]2)[C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)[CH:7]=2)=[O:4])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2763214Thiazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67496741HCID 67496741, compound

Product 1

HCID 67497569HCID 67497569, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a 20 ml vial were added (S)-2-amino-3-phenyl-N-(3-(pyridin-4-yl)phenyl)propanamide 34.1.D (75 mg, 0.19 mmole), thiazole-4-carbaldehyde (20 mg, 0.18 mmole), sodium triacetoxyborohydride (60 mg, 2.9 mmole), 5 ml of DCE, and DIEA (99 μl, 0.57 mmole). The reaction was stirred at room temperature for 1 hour. The reaction was then partitioned between 10 ml of water and 20 ml of DCM and the solvent was removed by rotary evaporation. The crude was purified using reverse phase preparative HPLC to give 34.8 mg of (S)-3-phenyl-N-(3-(pyridin-4-yl)phenyl)-2-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)propanamide 34.1 as a light yellow solid. LCMS ESI (pos.) m/e: 430.3 (M+1): 1H NMR (500 MHz, MeOH) δ ppm 8.89 (d, J=6.85 Hz, 2H), 8.32 (d, J=6.85 Hz, 2H), 8.11 (t, J=1.83 Hz, 1H), 7.67-7.79 (m, 1H), 7.50-7.64 (m, 2H), 7.22-7.34 (m, 5H), 4.29 (dd, J=9.41, 5.99 Hz, 1H), 3.81-3.94 (m, 2H), 3.34-3.43 (m, 3H), 3.21-3.27 (m, 1H), 3.05-3.18 (m, 2H), 1.57-1.75 (m, 5H), 1.29 (br. s., 2H).

Workup

  1. customThe reaction was then partitioned between 10 ml of water and 20 ml of DCM
  2. customthe solvent was removed by rotary evaporation
  3. customThe crude was purified

Sources & evidence

ORD record
ord-217a6b555c4e43f193e20691adea79fe
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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