Sodium Carbonate → HCID 59752560, compound

HRID 600094Notes

Reaction equation

[CH2:1]([N:8]1[C:17]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][C:11]=2[C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:26][C:27]([NH2:29])=[O:28].C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[CH2:1]([N:8]1[C:17]2[CH2:16][CH2:15][N:14]([CH2:26][C:27]([NH2:29])=[O:28])[CH2:13][CH2:12][C:11]=2[C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-benzyl-3-(4-chloro-phenyl)-1-pyridin-3-ylmethyl-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (Example 59, Step E; 0.05 mmol), 2-bromo-acetamide (8 mg), and Na2CO3 (15 mg) in acetone (2 mL) was stirred at 25° C. for 16 h. After concentration, purification by flash chromatography (2 M NH3/MeOH in CH2Cl2) provided the desired compound (6 mg). MS (ESI): exact mass calculated for C22H23ClN4O, 394.16. found, m/z 395.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.49-8.48 (m, 1H), 7.56-7.54 (m, 1H), 7.44-7.42 (m, 2H), 7.32-7.30 (m, 2H), 7.19-7.11 (m, 1H), 6.84-6.82 (m, 1H), 5.39 (s, 2H), 2.93-2.87 (m, 2H), 2.76-2.74 (m, 2H).

Workup

concentrationAfter concentration, purification by flash chromatography (2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-bdb11f2d104b464880c3558d0b06cb35
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897771B2

Reaction notes

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