Bis(2-chloroethyl) ether → HCID 66605475, compound

HRID 2410927Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[C:8]([C:18]4[CH:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=4)[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.Cl[CH2:26][CH2:27][O:28][CH2:29][CH2:30]Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH3:24][C:21]1[N:20]=[CH:19][C:18]([C:8]2[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]3[NH:12][C:13]4[C:5]([C:6]=3[CH:7]=2)=[CH:4][CH:3]=[C:2]([N:1]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH:14]=4)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 200 °C

Procedure

7-Amino-3-(6-methylpyridin-3-yl)-9H-carbazole-1-carboxamide (134 mg, 0.284 mmol), 1-chloro-2-(2-chloroethoxy)ethane (101 mg, 0.709 mmol) and Na2CO3 (180 mg, 1.703 mmol) were mixed with DMF (4 mL) in a sealed microwave vial. The mixture was heated in microwave at 200° C. for 2 hrs. The mixture was filtered and then purified using preparative HPLC to give titled product. MS (ESI) m/z 387.00 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.16 (s, 1H), 8.97 (s, 1H), 8.53 (s, 1H), 8.3 (s, 1H), 8.18 (s, 1H), 8.15 (dd, 1H, J=8.0, 2.5), 8.05 (d, 1H, J=8.5), 7.51 (s, 1H), 7.37 (d, 1H, J=8.2), 7.24 (s, 1H), 6.94 (d, 1H, J=8.6), 3.8 (m, 4H), 3.19 (m, 4H), 2.53(s, 3H).

Workup

filtrationThe mixture was filtered
custompurified

Sources & evidence

ORD record: ord-44e1003edeb640719efb800733bf7c2c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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