Benzaldehyde → N-{5-[5-(Benzylamino)-6-chloropyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamide

HRID 252704Notes

Reaction equation

HRID 252704 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].Cl[Si](C)(C)C>CN1C(=O)CCC1.C(O)(=O)C>[CH2:19]([NH:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6397ChlorotrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 86244450N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

Product 1

HCID 11501639N-{5-[5-(Benzylamino)-6-chloropyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamideYield 46.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (30 mg, 0.11 mmol), benzaldehyde (0.016 mL, 0.16 mmol) and sodium cyanoborohydride (13 mg, 0.21 mmol) were mixed in NMP (0.9 mL) and acetic acid (0.1 mL). Chlorotrimethylsilane (0.04 mL, 0.32 mmol) was added and the mixture was stirred overnight. The reaction product was purified by preparative HPLC (Method A) to give the title product (retention time 9.73 minutes; 19 mg); 1H NMR Spectrum: (DMSOd6) 12.13 (1H, s); 7.60 (1H, d); 7.38-7.30 (4H, m); 7.22 (1H, t); 6.80 (1H, d); 6.67 (1H, s); 4.47 (2H, s); 2.12 (3H, s); 2.03 (3H, s); Mass Spectrum: M+H+ 373 and 375.

Workup

  1. customThe reaction product was purified by preparative HPLC (Method A)

Sources & evidence

ORD record
ord-41f9b66c677d4434bd97f9876f554b7f
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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