HCID 66599980, compound → HCID 178507723, compound

HRID 1621370Notes

Reaction equation

HRID 1621370 reaction equation
O1CCCCC1[N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][C:12]=2[C:16]1[C:17]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([NH:29]C(=O)C)=[N:27][CH:28]=2)=[N:18][CH:19]=[CH:20][CH:21]=1>Cl>[N:11]1[C:12]([C:16]2[C:17]([NH:22][C:23]3[CH:28]=[N:27][C:26]([NH2:29])=[CH:25][CH:24]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:13]2[C:8]([NH:7][CH:15]=[N:14]2)=[N:9][CH:10]=1

Participants

3

Reactant 1

HCID 66599980HCID 66599980, compound

Product 1

HCID 178507723HCID 178507723, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(5-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)pyridin-2-yl)acetamide (18.8 mg, 44 μmol) in 5N aqueous HCl (1 mL) was heated at 95° C. for 1 h, after which time LCMS indicated conversion to desired product. The solution was made slightly alkaline with 5N aqueous NaOH (about pH 8) and the resulting precipitate was collected by filtration, washing with water, and dried to give N3-(3-(9H-purin-6-yl)pyridin-2-yl)pyridine-3,6-diamine (6.0 mg, 45% yield) as a dark solid. 1H NMR (d6-DMSO, 400 MHz) δ 12.17 (bs, 1H), 9.74 (d, 1H), 8.98 (s, 1H), 8.55 (s, 1H), 8.21 (m, 2H), 7.77 (dd, 1H), 6.89 (dd, 1H), 6.49 (d, 1H), 5.65 (bs, 3H); m/z (API-ES) 305, (M+H)+.

Sources & evidence

ORD record
ord-e642281c0b38436cb43a81c5fcef793a
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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