HCID 21913003, compound → HCID 21913584, compound

HRID 1352636Notes

Reaction equation

HRID 1352636 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]2[CH:26]=[N:27][CH:28]=[N:29][CH:30]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]3N=N[N:17]=[C:9]3[C:8]=2[N:18]=1)[CH3:2].C(OC1N(CCOCC2C=CN=CC=2)C2C(C)=C(C)N3N=NN=C3C=2N=1)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]2[CH:30]=[N:29][CH:28]=[N:27][CH:26]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21913003HCID 21913003, compoundHCID 21913309HCID 21913309, compound

Product 1

HCID 21913584HCID 21913584, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The method described in Part D of Example 109 was used with the following modification. The reaction was carried out in refluxing toluene, and 8-ethoxymethyl-5,6-dimethyl-7-[2-(3-pyrimidin-5-ylprop-2-ynyloxy)ethyl]-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridine (6.20 g, 15.3 mmol) was used in lieu of 8-ethoxy-5,6-dimethyl-7-[2-(pyridin-4-ylmethoxy)ethyl]-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridine. The crude product was purified by column chromatography on silica gel (200 g, eluting with 95:5 dichloromethane:methanol) to provide 0.852 g of 2-(ethoxymethyl)-6,7-dimethyl-1-{2-[(3-pyrimidin-5-ylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 122–124° C.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (200 g, eluting with 95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-35ae5af018424e43845f0015c46027da
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

Loading…