Pyridine → HCID 86651464, compound

HRID 1875485Notes

Reaction equation

[CH3:1][C:2]1([CH3:32])[C:11]2[C:10]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:9][CH:8]=[C:7]3[CH2:16][CH2:17][NH+:5]([C:6]=23)[CH:4]=[C:3]1/[CH:18]=[CH:19]/[CH:20]=[CH:21]/N(C1C=CC=CC=1)C(=O)C.[C:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]1([CH3:58])[C:50]2[C:49]([S:51]([O-:54])(=[O:53])=[O:52])=[CH:48][CH:47]=[C:46]3[CH2:55][CH2:56][NH+:44]([C:45]=23)[CH:43]=[C:42]1[CH3:57])([OH:35])=[O:34].N1C=CC=CC=1>C(OC(=O)C)(=O)C>[C:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]1([CH3:58])[C:50]2[C:45]3=[C:46]([CH2:55][CH2:56][NH+:44]3[CH:43]=[C:42]1/[CH:57]=[CH:21]/[CH:20]=[CH:19]/[CH:18]=[C:3]1\[C:2]([CH3:1])([CH3:32])[C:11]3[C:10]([S:12]([O-:15])(=[O:13])=[O:14])=[CH:9][CH:8]=[C:7]4[C:6]=3[N:5]\1[CH2:4][CH2:17][CH2:16]4)[CH:47]=[CH:48][C:49]=2[S:51]([OH:54])(=[O:53])=[O:52])([OH:35])=[O:34]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirring mixture of 6,6-dimethyl-5-((1E,3E)-4-(N-phenylacetamido)buta-1,3-dienyl)-1,2,3,6-tetrahydropyrrolo[3,2,1-ij]quinolinium-7-sulfonate and 6-(5-carboxypentyl)-5,6-dimethyl-1,2,3,6-tetrahydropyrrolo[3,2,1-ij]quinolinium-7-sulfonate in 5 mL acetic anhydride was added 5 mL pyridine. The reaction was heated to 110° C. for 2 hours. After cooling to room temperature the product was precipitated with ethyl acetate, washed with Et2O, and isolated by vacuum filtration. The final product was purified by reverse-phase HPLC yielding a blue solid. MS m/z calculated for C36H43N2O8S2 (M+H): 695.25. Found 695.3 (M+H, ESI+).

Workup

temperatureAfter cooling to room temperature the product
customwas precipitated with ethyl acetate
washwashed with Et2O
customisolated by vacuum filtration
customThe final product was purified by reverse-phase HPLC
customyielding a blue solid

Sources & evidence

ORD record: ord-09b52f050e7f4189a3f809a4c90432d8
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309059B2

Reaction notes

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