Diisopropylethylamine → HCID 68157481, compound

HRID 1892738Notes

Reaction equation

HRID 1892738 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][CH: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>[Cl-].[NH4+].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][CH: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

7

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 68156708HCID 68156708, compound

Product 1

HCID 68157481HCID 68157481, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

N,N-dimethylformamide (1.88 mL) was added to a vial containing 4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoic acid (122.0 mg, 0.28 mmol), ethyl 3-aminopropanoate hydrochloride (86.6 mg, 0.56 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (214.0 mg, 0.56 mmol). Diisopropylethylamine (0.25 mL, 1.41 mmol) was then added. After stirring for 4 hours, the reaction was diluted with saturated ammonium chloride and extracted three times with diethyl ether. The combined organics were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-25% ethyl acetate in heptane) afforded (+/−)-ethyl 3-(4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)propanoate (117 mg, 78% yield). 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. extractionextracted three times with diethyl ether
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (0-25% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6550af8108ef40a29a6049af0fdd46bb
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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