Methylamine → HCID 68283626, compound

HRID 1527161Notes

Reaction equation

HRID 1527161 reaction equation
[N+](C1C=CC(O[C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[CH:14]2)=[O:12])=CC=1)([O-])=O.[CH3:32][NH2:33]>C1COCC1>[CH2:25]([O:24][C:22]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]([C:11](=[O:12])[NH:33][CH3:32])[CH:14]=1)=[O:23])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68284269HCID 68284269, compound

Product 1

HCID 68283626HCID 68283626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of indole-1,3-dicarboxylic acid 3-benzyl ester 1-(4-nitro-phenyl)ester (45 mg, 0.108 mmol) in dry THF (1 mL) was added methylamine (2 M in THF, 270 μl, 0.54 mmol) and the reaction was stirred at RT for 15 min. The mixture was concentrated and the residue was taken up in Et2O and filtered to give the desired compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.52; MS (LC/MS): 309.1 [M+H]+, 331.1 [M+Na]+, 639.2 [2M+Na]+, 353.2 [M+HCOO]−; tR (HPLC conditions a): 3.86 min.

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8eb02e350c4e4a8f8fb01918d8f9c0fe
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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