Pyridine → HCID 172930687, compound

HRID 612307Notes

Reaction equation

HRID 612307 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([OH:10])=O)[N:6]=1.CS(Cl)(=O)=O.C(N(CC)C(C)C)(C)C.[NH2:28][C@@H:29]1[C:55](=[O:56])[N:31]2[C:32]([C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)=[O:44])=[C:33]([C@@H:36]3[CH2:40][CH2:39][C:38]([CH3:42])([CH3:41])[O:37]3)[CH2:34][S:35][C@H:30]12.N1C=CC=CC=1>CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([NH:28][C@@H:29]2[C:55](=[O:56])[N:31]3[C:32]([C:43]([O:45][CH2:46][C:47]4[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=4)=[O:44])=[C:33]([C@@H:36]4[CH2:40][CH2:39][C:38]([CH3:41])([CH3:42])[O:37]4)[CH2:34][S:35][C@H:30]23)=[O:10])[N:6]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 53642024HCID 53642024, compound

Product 1

HCID 172930687HCID 172930687, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(2-Aminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid (13 mg, 0.065 mmol) in DMF (2 ml) was treated with methanesulphonyl chloride (5 μl, 0.064 mmol) and N,N-diisopropylethylamine (11 μl, 0.063 mmol) as described in Example 7 (a). This was then treated successively with a solution of the amine from Example 29 (e) (25 mg, 0.060 mmol) in DMF (2 ml) and pyridine (5 μl, 0.062 mmol). After work-up the product was purified by chromatography on silica gel eluting with 50, 70 and 100% ethyl acetate in hexane to yield the title compound (25 mg, 70%) as a yellow foam; νmax (CH2Cl2) 3389, 1784, 1722, 1690, 1607 and 1516 cm-1 ; δH (CDCl3, 250 MHz) 1.23 (3 H, s), 1.29 (3 H, s), 1.61-1.84 (3 H, m), 2.31 (1 H, m), 3.40 and 3.63 (2 H, ABq, J 18.7 Hz), 3.81 (3 H, s), 4.20 (3 H, s), 4.99 (1 H, d, J 4.8 Hz), 5.05 (1 H, dd, J 8.1, 8.1 Hz), 5.13 and 5.23 (2 H, ABq, J 11.8 Hz), 5.90 (1 H, dd, J 8.9, 4.8 Hz), 6.90 (2 H, d, J 8.7 Hz), 7.23 (1 H, s), 7.34 (2 H, d, J 8.7 Hz), 7.50 (2 H, br s, exch.) and 7.68 (1 H, br d, J 8.9 Hz, exch). [Mass spectrum: +ve ion (ammonia) MH+ (602)].

Workup

  1. customAfter work-up the product was purified by chromatography on silica gel eluting with 50, 70 and 100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8bdbd85c0d684b808cb31358e59ea525
Source dataset
uspto-grants-1999_12
Patent number
US06001997

Reaction notes

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