2-Bromoethylamine → HCID 22391938, compound

HRID 1072253Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([CH2:15][C:5]2=[C:4]([NH2:17])[C:3]=1[C:18]#[N:19])=[CH:13][CH:12]=[C:11]([OH:16])[CH:10]=3.Br[CH2:21][CH2:22][NH2:23].BrCCOCC>>[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([CH2:15][C:5]2=[C:4]([NH2:17])[C:3]=1[C:18]#[N:19])=[CH:13][CH:12]=[C:11]([O:16][CH2:21][CH2:22][NH2:23])[CH:10]=3

Participants

Reactant 3

HCID 78512-Bromoethylamine

HCID 611412-Bromoethyl ethyl ether

HCID 10106333HCID 10106333, compound

Product 1

HCID 22391938HCID 22391938, compound

Procedure

2,4-diamino-8-(2-aminoethoxy)-5H-chromeno[2,3-b]pyridine-3-carbonitrile was prepared from 2,4-diamino-8-hydroxy-5H-chromeno[2,3-b]pyridine-3-carbonitrile in the same manner as described in Example 10 using 2-bromoethylamine in lieu of 2-bromoethyl-ethylether. The product was isolated as a tan solid (167 mg, 51% yield). 1H NMR (400 MHz, DMSO) δ 8.180 (bs, 2H), 7.100 (d, 1H), 6.762 (d, 1H), 6.646 (bs, 1H), 4.154 (t, 2H), 3.573 (s, 2H), 3.155 (t, 2H); m/z 398 (M+H). TNFα release assay IC50: 6.9 μM; Rat LPS Assay 88% inhibition at 20 mpk (IP).

Sources & evidence

ORD record: ord-d2e99eb250f34defba81cc9701c5c6c4
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06909001B2

Reaction notes

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