Bromoacetic Acid → HCID 10425628, compound

HRID 1072254Notes

Reaction equation

HRID 1072254 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][C:22]([OH:24])=[O: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][C:22]([OH:24])=[O:23])[CH:10]=3

Participants

4

Reactant 3

HCID 6227Bromoacetic AcidHCID 611412-Bromoethyl ethyl etherHCID 10106333HCID 10106333, compound

Product 1

HCID 10425628HCID 10425628, compound

Procedure

[(2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-8-yl)oxy]acetic acid 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 bromoacetic acid in lieu of 2-bromoethyl-ethylether. The product was isolated as a tan solid (110.6 mg, 31% yield). 1H NMR (400 MHz, DMSO) δ 7.030 (d, 1H), 6.640 (d, 1H), 6.516 (d, 1H), 6.474 (bs, 2H), 6.278 (bs, 2H), 4.633 (s, 2H), 3.543 (s, 2H); m/z 427 (M+H).

Sources & evidence

ORD record
ord-f063489040c4459eb7113f4a1a5d1146
Source dataset
uspto-grants-2005_06
Patent number
US06909001B2

Reaction notes

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