4-Bromobenzoic acid → HCID 118357283, compound

HRID 2273607Notes

Reaction equation

HRID 2273607 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=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.[NH2:44][C:45]1[CH:64]=[CH:63][C:48]([CH2:49][N:50]2[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH2:51]2)=[CH:47][CH:46]=1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:44][C:45]2[CH:46]=[CH:47][C:48]([CH2:49][N:50]3[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:60])([CH3:62])[CH3:61])=[O:57])[CH2:52][CH2:51]3)=[CH:63][CH:64]=2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 114644-Bromobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12045001tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate

Product 1

HCID 118357283HCID 118357283, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Bromobenzoic acid (1, 685.0 mg, 3.4 mmol) and HATU (1298.1 mg, 3.4 mmol) are partially dissolved in DMF (10 mL) at rt. DIEA (560 μL, 3.4 mmol) is added to this mixture to give a pale yellow solution. After stirring at rt for 30 min, tert-butyl 4-(4-aminobenzyl)piperazine-1-carboxylate (2, 992.9 mg, 3.4 mmol) is added and the resulting reaction mixture is heated at 60° C. for 20 h, allowed to cool to rt, and poured into water (100 mL). This mixture is extracted with Et2O (3×150 mL). The combined organic extracts are evaporated to dryness to give a white solid, which is washed with water (50 mL) and dried in vacuo. This material is used in the next synthetic step without further purification. HPLC: tR 1.67 min (method 1). LC-MS m/z calcd for C23H2879BrN3O3 ([M]+), 473. found, 474 ([M+H]+). 1H NMR (CD3OD): δ 1.46 (s, 9H), 2.96 (m, 4H), 3.59 (m, 4H), 4.05 (br s, 2H), 7.46 (m, 2H), 7.69 (m, 2H), 7.78 (m, 2H), 7.85 (m, 2H).

Workup

  1. customto give a pale yellow solution
  2. customthe resulting reaction mixture
  3. temperatureis heated at 60° C. for 20 h
  4. temperatureto cool to rt
  5. extractionThis mixture is extracted with Et2O (3×150 mL)
  6. customThe combined organic extracts are evaporated to dryness
  7. customto give a white solid, which
  8. washis washed with water (50 mL)
  9. customdried in vacuo
  10. customThis material is used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-1d3f288bd77542fb958fcb18598c3afa
Source dataset
uspto-grants-2015_09
Patent number
US09125904B1

Reaction notes

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