4-tert-Butylbenzoic acid → HCID 178444042, compound

HRID 1623019Notes

Reaction equation

HRID 1623019 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C@@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[NH:28][CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:34][CH:33]=3)[N:31]=2)=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:14][C@@H:15]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[NH:28][CH:29]=[C:30]([C:32]4[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:36][CH:37]=4)[N:31]=3)=[CH:25][CH:26]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:11])=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 74034-tert-Butylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178444043HCID 178444043, compound

Product 1

HCID 178444042HCID 178444042, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(tert-butyl)benzoic acid (25 mg, 0.14 mmol), (S)-methyl 2-amino-3-(4-(4-(4-(heptyloxy)phenyl)-1H-imidazol-2-yl)phenyl)propanoate (55 mg, 0.13 mmol), and TEA (53 μl, 0.38 mmol) in DMF (1 mL) was added HATU (53 mg, 0.14 mmol). The reaction mixture was stirred at RT for 2 h, diluted in DCM, and washed aq. NaHCO3. The organic layer was dried, concentrated and purified by chromatography (EA/hexane) to provide 14 mg (17%) of methyl (S)-2-(4-(tert-butyl)benzamido)-3-(4-(4-(4-(heptyloxy)phenyl)-1H-imidazol-2-yl)phenyl)propanoate. LCMS-ESI (m/z) calculated for C37H45N3O4: 595.8; found 596.4 [M+H]+, tR=2.33 min. (Method 8).

Workup

  1. washwashed aq. NaHCO3
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by chromatography (EA/hexane)

Sources & evidence

ORD record
ord-a32b5fb866264427b36a5608abb08bd9
Source dataset
uspto-grants-2014_07
Patent number
US08778923B2

Reaction notes

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