Sodium Nitrite → 7-(Sec.-butylamino)-5-methyl[1,2,3]thiadiazolo[5,4-b]pyridine-6-carboxylic acid, ethyl ester

HRID 1658525Notes

Reaction equation

HRID 1658525 reaction equation
[NH2:1][C:2]1[C:3]([NH:15][CH:16]([CH2:18][CH3:19])[CH3:17])=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([CH3:9])=[N:6][C:7]=1[SH:8].[N:20]([O-])=O.[Na+]>C(O)(=O)C>[CH:16]([NH:15][C:3]1[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([CH3:9])[N:6]=[C:7]2[S:8][N:20]=[N:1][C:2]=12)([CH2:18][CH3:19])[CH3:17]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 178469256HCID 178469256, compound

Product 1

HCID 1317103447-(Sec.-butylamino)-5-methyl[1,2,3]thiadiazolo[5,4-b]pyridine-6-carboxylic acid, ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

By treating 5-amino-4-sec.butylamino-6-mercapto-2-methylpyridine-3-carboxylic acid, ethyl ester with sodium nitrite in acetic acid as described in Example 1 e, 7-(sec.-butylamino)-5-methyl[1,2,3]thiadiazolo[5,4-b]pyridine-6-carboxylic acid, ethyl ester is obtained, yield 72% m.p. 48°-50° (ether).

Sources & evidence

ORD record
ord-4beddf14c53c4a7ab00b716f6a2c5664
Source dataset
uspto-grants-1976_06
Patent number
US03965108

Reaction notes

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