Water → HCID 178458738, compound

HRID 128710Notes

Reaction equation

HRID 128710 reaction equation
[CH:1]([O:4][C:5]1[C:9]2[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][C:8]=2[S:7][C:6]=1[C:21]([OH:23])=O)([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:36][C:37]1[NH:41][N:40]=[N:39][N:38]=1.O>CN(C=O)C>[NH:38]1[C:37]([NH:36][C:21]([C:6]2[S:7][C:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]=3[C:5]=2[O:4][CH:1]([CH3:3])[CH3:2])=[O:23])=[N:41][N:40]=[N:39]1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 19374945HCID 19374945, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178458738HCID 178458738, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 1.43 g (4.2 mmol) of 3-isopropoxy-5-tert-butoxycarbonyl-6,7-dihydro-4H-thieno[3,2-c]pyridine-2-carboxylic acid in 15 mL of DMF were added 1.07 g (6.6 mmol) of 1,1'-carbonyldiimidazole. The reaction mixture was heated at 85° C. for 2 hours. 5-Aminotetrazole (0.655 g, 7.7 mmol) was added to the reaction mixture in one portion, and the mixture was stirred at 85° C. for 8 hours. The solution was cooled to 24° C. and stirred at that temperature for 18 hours. The reaction mixture was diluted by addition of 100 mL of water and was extracted three times with 50 mL portions of chloroform. The extracts were washed with 50 mL of 2N HCl, water, brine, dried over Na2SO4, and concentrated to dryness by evaporation of the solvent under reduced pressure. The residue was crystallized from 500 mL of diethyl ether to give 1.02 g of 3-isopropoxy-5-tert-butoxycarbonyl-6,7-dihydro-4H-thieno[3,2-c]pyridine-2-carboxylic acid (1H-tetrazol-5-yl) amide, mp 189°-191° C.

Workup

  1. temperatureThe solution was cooled to 24° C.
  2. stirringstirred at that temperature for 18 hours
  3. extractionwas extracted three times with 50 mL portions of chloroform
  4. washThe extracts were washed with 50 mL of 2N HCl, water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness by evaporation of the solvent under reduced pressure
  7. customThe residue was crystallized from 500 mL of diethyl ether

Sources & evidence

ORD record
ord-c7f4cbc5025142b0ac6212b4fd22f1e6
Source dataset
uspto-grants-1995_11
Patent number
US05464855

Reaction notes

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