1-Pyrrolidineethanamine → HCID 69637159, compound

HRID 1825732Notes

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

Participants

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

temperaturethe mixture heated at the same temperature for an additional time of 20 h
temperatureto cool to room temperature
customthe solvent removed under reduced pressure
additionThe residue was treated with water
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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