Diisopropylethylamine → HCID 68178610, compound

HRID 1892741Notes

Reaction equation

HRID 1892741 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([CH3:31])[C:21]=1[N:22]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[N:23]1)[O:5][C@H:6]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)[CH2:7][CH2:8][CH3:9].Cl.[NH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([CH3:31])[C:21]=1[N:22]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[N:23]1)[O:5][C@H:6]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:16])=[CH:17][CH:18]=1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68156707HCID 68156707, compound

Product 1

HCID 68178610HCID 68178610, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dimethylformamide (17.6 mL) was added to a vial containing (S)-4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoic acid (6.1 g, 14.1 mmol), ethyl 3-aminopropanoate hydrochloride (4.33 g, 28.2 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (10.7 g, 28.2 mmol). Diisopropylethylamine (12.3 mL, 70.5 mmol) was then added. The reaction was stirred for 1 h, and was then concentrated. Purification by column chromatography (0-30% ethyl acetate in heptane) afforded (S)-ethyl 3-(4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)propanoate (7.07 g, 94% yield) as a colorless gum. 1H NMR (400 MHz, CDCl3, δ): 7.87 (s, 1H), 7.73 (d, J=8.0 Hz, 2H), 7.65 (s, 1H), 7.39 (d, J=8.2 Hz, 2H), 6.84 (d, J=5.9 Hz, 1H), 6.57 (s, 2H), 5.15 (dd, J=7.8, 5.1 Hz, 1H), 4.17 (q, J=7.1 Hz, 2H), 3.71 (q, J=6.0 Hz, 2H), 2.63 (t, J=5.7 Hz, 2H), 2.04-1.91 (m, 1H), 1.88 (s, 6H), 1.86-1.71 (m, 1H), 1.58-1.33 (m, 2H), 1.26 (t, J=7.0 Hz, 3H), 0.96 (t, J=7.4 Hz, 3H). MS (M+1): 532.

Workup

  1. concentrationwas then concentrated
  2. customPurification by column chromatography (0-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-183643ce73504e06b32bff4f4b6a1d69
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

Loading…