7-Methoxy-1-oxo-1H-pyrimido[6,1-b]benzthiazole-4-carboxylic acid → HCID 178487336, compound

HRID 224352Notes

Reaction equation

HRID 224352 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]3[C:13](=[O:14])[N:12]=[CH:11][C:10]([C:15]([OH:17])=O)=[C:8]3[S:9][C:5]=2[CH:4]=1.O.[NH2:21][C:22]1[NH:26][N:25]=[N:24][N:23]=1>CN(C)C=O>[NH:23]1[C:22]([NH:21][C:15]([C:10]2[CH:11]=[N:12][C:13](=[O:14])[N:7]3[C:6]4[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[S:9][C:8]=23)=[O:17])=[N:26][N:25]=[N:24]1

Participants

4

Reactant 2

HCID 233327897-Methoxy-1-oxo-1H-pyrimido[6,1-b]benzthiazole-4-carboxylic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 178487336HCID 178487336, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5.52 g. 7-Methoxy-1-oxo-1H-pyrimido[6,1-b]benzthiazole-4-carboxylic acid (prepared according to Example 1) in 150 ml. dimethylformamide are mixed with 7.14 g. N,N'-carbonyldiimidazole. The reaction mixture is subsequently stirred for 90 minutes at 100° C. and for 1 hour at ambient temperature, then mixed with 2.26 g. 5-aminotetrazole monohydrate and again heated for 3 hours at 100° C. The solvent is substantially removed in vacuo and the residue stirred with water. The precipitate consists of 5.2 g. N-(5-tetrazolyl)-7-methoxy-1-oxo-1H-pyrimido[6,1-b]benzthiazole-4-carboxamide (75.7% of theory); m.p. 234°-235° C. (recrystallized from nitromethane).

Workup

  1. additionmixed with 2.26 g
  2. customThe solvent is substantially removed in vacuo
  3. stirringthe residue stirred with water
  4. customm.p. 234°-235° C. (recrystallized from nitromethane)

Sources & evidence

ORD record
ord-2696d629127747838eea9fdd3be8e559
Source dataset
uspto-grants-1980_11
Patent number
US04232024

Reaction notes

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