4-Chloromethylthiazol-2-ylamine → rac-2-Amino-6-{[(2-amino-1,3-thiazol-4-yl)methyl]sulfanyl}-4-(tetrahydro-2H-pyran-2-yl)-pyridine-3,5-dicarbonitrile

HRID 1873611Notes

Reaction equation

HRID 1873611 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([C:16]#[N:17])=[C:4]([SH:18])[N:3]=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([NH2:26])[S:24][CH:25]=1.C(=O)(O)[O-].[Na+].NC1C(C#N)=C(C2CCCCO2)C(C#N)=C(SCC2N=C(C3C=CC(Cl)=CC=3)SC=2)N=1>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:20][C:21]2[N:22]=[C:23]([NH2:26])[S:24][CH:25]=2)[N:3]=1

Participants

6

Reactant 4

HCID 732294-Chloromethylthiazol-2-ylamineHCID 516892Sodium BicarbonateHCID 24959059Rac-2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(tetrahydro-2h-pyran-2-yl)-pyridine-3,5-dicarbonitrileHCID 178510477HCID 178510477, compound

Product 1

HCID 87548657rac-2-Amino-6-{[(2-amino-1,3-thiazol-4-yl)methyl]sulfanyl}-4-(tetrahydro-2H-pyran-2-yl)-pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.14 mmol) of the compound from Example 31A, 39 mg (0.21 mmol) of 4-(chloromethyl)-1,3-thiazol-2-amine and 48 mg (0.58 mmol) of sodium bicarbonate in 2.0 ml of dry DMF are reacted analogously to the preparation of the compound of Example 14.

Sources & evidence

ORD record
ord-443d51d92dc846279f633e268e4993b8
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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