Diisopropylethylamine → N-(1,3-Thiazol-2-yl)pyridin-2-amine 21

HRID 1355455Notes

Reaction equation

HRID 1355455 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:4]=1.Cl.[C:18]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)(=[O:21])[CH2:19][OH:20].C(N(C(C)C)CC)(C)C>CS(C)=O.O>[OH:20][CH2:19][C:18]([N:22]1[CH2:27][CH2:26][N:25]([CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]3[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=3)[CH:4]=2)[CH2:24][CH2:23]1)=[O:21]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11161046HCID 11161046, compoundHCID 185068832-Hydroxy-1-(piperazin-1-yl)ethan-1-one hydrochloride

Product 1

HCID 5329334N-(1,3-Thiazol-2-yl)pyridin-2-amine 21

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-{[4-(Chloromethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (180 mg, 0.72 mmole) and 1-glycoloylpiperazine hydrochloride (259 mg, 1.44 mmole) were combined in DMSO (2 mL). To this was added diisopropylethylamine (0.38 mL, 2.15 mmole) at RT. After 3 hr the mixture was diluted with H2O and extracted with EtOAc (3×g). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 5-15% EtOH/EtOAc then 5-10% MeOH/CHCl3) gave the title compound as a pale yellow solid: 1H NMR (d6-DMSO) δ12.19 (s, 1H), 8.33 (d, 1H, J=5.1 Hz), 8.32 (s, 1H), 7.14 (s, 1H), 7.04 (d, 1H, J=5.2 Hz), 4.54 (t, 1H, J=5.6 Hz), 4.08 (d, 2H, J=5.6 Hz), 3.55 (s, 2H), 3.49 (s, 2H), 3.36 (s, 2H), 2.38 (s, 4H); MS [M+H]+=359.1285.

Workup

  1. extractionextracted with EtOAc (3×g)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3046120b786542d0bfadcc3b11645a04
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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