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1-Pyrrolidineethanamine → HCID 69637159, compound

HRID 1825732
Notes
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Reaction equation

HRID 1825732 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8](/[CH:13]=[C:14]3\[S:15][C:16]4[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=4[NH:18][C:19]\3=[O:20])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)(O)=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:37][CH2:38][CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>CN(C)C=O>[N:40]1([CH2:39][CH2:38][NH:37][C:1]([C:4]2[CH:12]=[C:11]3[C:7]([C:8](/[CH:13]=[C:14]4\[S:15][C:16]5[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=5[NH:18][C:19]\4=[O:20])=[CH:9][NH:10]3)=[CH:6][CH:5]=2)=[O:2])[CH2:44][CH2:43][CH2:42][CH2:41]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 682631,1'-CarbonyldiimidazoleHCID 69637201HCID 69637201, compound

Product 1

HCID 69637159HCID 69637159, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (Z)-2-[(6-carboxyindol-3-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one (0.5 g, 1.5 mmol) in dry N,N-dimethylformamide (30 ml), 1,1′-carbonyldiimidazol (0.24 g, 1.5 mmol) was added under nitrogen atmosphere, and the mixture was heated at 40° C. for 1 h. Then N-(2-aminoethyl)pyrrolidine (0.34 g, 2.98 mmol) was added and the mixture heated at the same temperature for an additional time of 20 h. The reaction was allowed to cool to room temperature and the solvent removed under reduced pressure. The residue was treated with water and the yellow precipitate was crystallized from N,N-dimethylformamide/water to yield 0.31 g (48%) of the entitled product.

Workup

  1. temperaturethe mixture heated at the same temperature for an additional time of 20 h
  2. temperatureto cool to room temperature
  3. customthe solvent removed under reduced pressure
  4. additionThe residue was treated with water
  5. customthe yellow precipitate was crystallized from N,N-dimethylformamide/water

Sources & evidence

ORD record
ord-9dab16f550824dfea10941a35432cf1c
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07049312B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes