4-amino-8-iodo-N-propyl-cinnoline-3-carboxamide → HCID 23629997, compound

HRID 2375606Notes

Reaction equation

HRID 2375606 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14].C[Sn](C)(C)[C:21]1[CH:22]=[N:23][CH:24]=[C:25]([C:27]([N:29]2[CH2:32][CH2:31][CH2:30]2)=[O:28])[CH:26]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:21]3[CH:22]=[N:23][CH:24]=[C:25]([C:27]([N:29]4[CH2:30][CH2:31][CH2:32]4)=[O:28])[CH:26]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14]

Participants

3

Reactant 2

HCID 140123274-amino-8-iodo-N-propyl-cinnoline-3-carboxamideHCID 59693892HCID 59693892, compound

Product 1

HCID 23629997HCID 23629997, compoundYield 44%

Procedure

Using method D, 4-amino-8-iodo-N-propyl-cinnoline-3-carboxamide (100 mg, 0.28 mmol) and 3-trimethylstannyl-5-(azetidin-1-ylcarbonyl)-pyridine (182 mg, of 80%, 0.45 mmol) were reacted to afford the title compound (48 mg, 44.0% yield) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.00 (s, 1H), 8.89 (s, 1H), 8.51 (br, 1H), 8.40 (s, 1H), 7.96 (d, J=7.0 Hz, 1H), 7.72-7.88 (m, 2H), 4.46 (br, 2H), 4.28 (br, 2H), 3.48 (q, J=6.7 Hz, 2H), 2.40 (m, J=7.8 Hz, 2H), 1.69 (m, J=7.3 Hz, 2H), 1.02 (t, J=7.4 Hz, 3H). MS APCI, m/z=391 (M+H). HPLC 1.74 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8f61c220376140908cb6e742dbe30b9f
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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