1-Pyrrolidineethanamine → HCID 68650132, compound

HRID 1771899Notes

Reaction equation

HRID 1771899 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([O:13]C)=O)[C:5]([C:6]([OH:8])=O)=[C:4]([CH3:15])[C:3]=1[N+:16]([O-])=O.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.[N:52]1([CH2:57][CH2:58][NH2:59])[CH2:56][CH2:55][CH2:54][CH2:53]1>C1COCC1>[NH2:16][C:3]1[C:4]([CH3:15])=[C:5]2[C:9](=[CH:10][C:2]=1[NH2:1])[C:11](=[O:13])[N:59]([CH2:58][CH2:57][N:52]1[CH2:56][CH2:55][CH2:54][CH2:53]1)[C:6]2=[O:8]

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86677138HCID 86677138, compound

Product 1

HCID 68650132HCID 68650132, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-6-(methoxycarbonyl)-2-methyl-3-nitrobenzoic acid (380 mg, 1.0 mmol), HATU (114 mg, 1.0 mmol) and DIPEA (129 mg, 1.0 mmol) in THF (20 mL) was added 2-(pyrrolidin-1-yl)ethanamine (114 mg, 1.0 mmol) and stirred at RT for overnight. The reaction mixture was evaporated in vacuo and the residue was triturated with MeOH (10 mL). The yellow precipitate was isolated by filtration and dried to afford the title compound (300 mg) as a yellow solid.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was triturated with MeOH (10 mL)
  3. customThe yellow precipitate was isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-6d545715cb14467e8d70ef286300ef08
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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