2-Bromoethanol → HCID 10266683, compound

HRID 1072255Notes

Reaction equation

HRID 1072255 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][OH: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][OH:23])[CH:10]=3

Participants

4

Reactant 3

HCID 108982-BromoethanolHCID 611412-Bromoethyl ethyl etherHCID 10106333HCID 10106333, compound

Product 1

HCID 10266683HCID 10266683, compound

Procedure

2,4-diamino-8-(2-hydroxyethoxy)-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-bromoethanol in lieu of 2-bromoethyl-ethylether. The product was isolated as a tan solid (120 mg, 35% yield). 1H NMR (400 MHz, DMSO) δ 7.025 (d, 1H), 6.670 (d, 1H), 6.550 (d, 1H), 3.931 (t, 2H), 3.662 (t, 2H), 3.546 (s, 2H); m/z 413 (M+H).

Sources & evidence

ORD record
ord-b6ea95aebc9043b7b0d739c1a8b1e54a
Source dataset
uspto-grants-2005_06
Patent number
US06909001B2

Reaction notes

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