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4-Formylbenzoic acid → HCID 59340335, compound

HRID 907632
Notes
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Reaction equation

HRID 907632 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:36][CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][CH:42]([O:45][C:46](=[O:60])[NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([NH:36][CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][CH:42]([O:45][C:46](=[O:60])[NH:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:41][CH2:40]2)=[O:3])=[CH:5][CH:6]=1)=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 120884-Formylbenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53319786Biphenyl-2-ylcarbamic acid 1-(2-aminoethyl)piperidin-4-yl ester

Product 1

HCID 59340335HCID 59340335, compound
Yield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-carboxybenzaldehyde (0.95 g, 6.35 mmol) and HATU (3.02 g, 7.94 mmol) in 55 mL of DCM was stirred at room temperature for 1 hour and then biphenyl-2-ylcarbamic acid 1-(2-aminoethyl)piperidin-4-yl ester (3 g, 5.29 mmol; prepared as described in Preparation 7) and DIPEA (4.6 mL, 26.45 mmol) were added. The resulting mixture was stirred at room temperature for 2 hours and then diluted with 100 mL of DCM and washed with saturated sodium bicarbonate (150 mL) and brine (150 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 2.3 g of the title intermediate (92% yield), which was suitable for use without further purification.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. washwashed with saturated sodium bicarbonate (150 mL) and brine (150 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0aece4df32994d3b95a696d388796ece
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08013152B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes