HCID 66718650, compound → HCID 66718967, compound

HRID 1645309Notes

Reaction equation

HRID 1645309 reaction equation
[Cl-].NC1C=CC2N3C4C=CC=CC=4[N+](CC)=C3C=CC=2C=1.[CH3:22][C:23]1[CH:24]=[CH:25][C:26]2[S:30][C:29](/[CH:31]=[CH:32]/[C:33]3[CH:38]=[C:37]([NH2:39])[C:36]([Cl:40])=[CH:35][C:34]=3Cl)=[N:28][C:27]=2[CH:42]=1>CCO>[Cl-:40].[NH2:39][C:37]1[C:36]([Cl:40])=[CH:35][C:34]2[N+:28]3[C:27]4[CH:42]=[C:23]([CH3:22])[CH:24]=[CH:25][C:26]=4[S:30][C:29]=3[CH:31]=[CH:32][C:33]=2[CH:38]=1

Participants

4

Reactant 2

HCID 66718650HCID 66718650, compoundHCID 86646361HCID 86646361, compound

Product 1

HCID 66718967HCID 66718967, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The amino precursors of ABQ-38 and ABQ-95, (E)-7-ethyl-2-(5-amino-2-chlorostyryl)benzimidazole IIv and (E)-5-methyl-2-(5-amino-2,4-dichlorostyryl)benzothiazole IId, respectively, were prepared by the reduction of the corresponding nitro derivatives with hydrazine in the presence of nickel boride in dry methanol, see FIG. 3. (E)-7-ethyl-2-(5-amino-2-chlorostyryl)benzimidazole IIv was photocyclized as described (BQS Method 1) to give 3-amino-7-ethylbenzimidazo[3,2-a]quinolinium chloride (ABQ-38) as a yellow solid: 1H NMR (500.13 MHz, DMSO-d6): δ ppm 9.05 (d, 1H, J=8.50 Hz), 8.88 (d, 1H, J=9.0 Hz), 8.56 (d, 1H, J=9.5 Hz, 8.27 (d, 1H, J=8.5 Hz), 8.23 (d, 1H, J=9.50 Hz), 7.90 (t, 1H, J=7.5 Hz), 7.81 (t, 1H, J=7.5 Hz), 7.43 (dd, 1H, J=8.5, 2.5), 7.27 (d, 1H, J=2.5 Hz), 4.83 (q, 2H, J=7.0 Hz), 1.48 (t, 3H, J=7.0 Hz); UV-vis (95% EtOH) λmax/nm (e): 409 (1410), 351 (8104), 336 (9815) and 271 (20866); HRMS calcd for C17H16N3 (compound without the chloride counter ion) 262.1, found by ESI at m/z 261.9. (E)-5-methyl-2-(5-amino-2,4-dichlorostyryl)benzothiazole IId was photocyclized as described (BQS Method 1) to give 3-amino-2-chloro-10-methylbenzothiazolo[3,2-a]quinolinium chloride (ABQ-95) as a yellow solid: 1H NMR (500.13 MHz, DMSO-d6): δ ppm 9.17 (s, 1H), 8.92 (s, 1H), 8.63(AB quartet, 2H, J=9.5 Hz), 8.48 (d, 1H, J=8.5 Hz), 7.76 (d, 1H, J=8.5 Hz), 7.53 (s, 1H), 6.50 (m, 2H), 2.70 (s, 3H); UV-vis (95% EtOH) λmax/nm (e): 429 (4417), 380 (10 387), 282 (22 568) and 214(2650); HRMS calcd for C16H12ClN2S 299.0 (without the chloride counter ion), found by ESI at m/z 299.0 M+.

Sources & evidence

ORD record
ord-4f7243774ad94aa0b8c5e450b59f258d
Source dataset
uspto-grants-2012_02
Patent number
US08124770B2

Reaction notes

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