N,N-Dimethyl-1,3-propanediamine → 3-Cyano-1-[4-(3-dimethylamino-propylamino)-benzoyl]-pyrrolo[1,2-a]quinoline

HRID 720425Notes

Reaction equation

HRID 720425 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH2:30]>>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([NH:30][CH2:29][CH2:28][CH2:27][N:26]([CH3:31])[CH3:25])=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

Product 1

HCID 218921633-Cyano-1-[4-(3-dimethylamino-propylamino)-benzoyl]-pyrrolo[1,2-a]quinoline

Procedure

The title compound was prepared as described for Example 21, using 3-cyano-(4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline (65 mg, 0.206 mmol) and N1,N1-dimethyl-propane-1,3-diamine (200 mg, 1.96 mmol) and yielded 68 mg (83%). 1H NMR (CDCl3): 7.98 (m, 2H), 7.81 (dd, J=7.5, 1.8 Hz, 1H), 7.55 (m, 4H), 7.31 (s, 1H), 6.63 (d, J=9.0 Hz, 2H), 5.78 (s, broad, 1H), 3.34 (m, 2H), 2.51 (t, J=6.3 Hz, 2H), 2.31 (s, 6H), 1.85 (m, 2H).

Workup

  1. customyielded 68 mg (83%)

Sources & evidence

ORD record
ord-772c561a30b3479a93b5ce8f8e9274c4
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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