Aminoacetaldehyde dimethyl acetal → HCID 20605658, compound

HRID 481065Notes

Reaction equation

HRID 481065 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]2[C:10](SC)=[N:11][CH2:12][CH2:13][C:8]=2[N:7]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH:6]=1)=[O:4].[CH3:27][O:28][CH:29]([O:32][CH3:33])[CH2:30][NH2:31]>CO>[CH3:1][O:2][C:3]([C:5]1[C:9]2[C:10]([NH:31][CH2:30][CH:29]([O:32][CH3:33])[O:28][CH3:27])=[N:11][CH2:12][CH2:13][C:8]=2[N:7]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 20605659HCID 20605659, compound

Product 1

HCID 20605658HCID 20605658, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round bottom flask are 4-Methylsulfanyl-1-[2-(4-nitro-phenyl)-ethyl]-6,7-dihydro-1H-pyrrolo[3,2-C]pyridine-3-carboxylic acid methyl ester (25.33 mmol), amino acetaldhyde dimethyl acetal (63.32 mmol) and 125 mL MeOH combined (a part “oiled-out” that later went into solution) and stirred at RT for 20 hours. The solvent is evaporated in vacuo yielding 4-(2,2-Dimethoxy-ethylamino)-1-[2-(4-nitro-phenyl)-ethyl]-6,7-dihydro-1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid methyl ester, 11.56 g, as a yellow oil/solid that is used without purification.

Workup

  1. customIn a round bottom flask are
  2. customThe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-a87f9e94e55c44a887d207831674fabc
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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