Hydrochloric Acid → HCID 10086633, compound

HRID 1361027Notes

Reaction equation

HRID 1361027 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.C1C=NC2N(O)N=NC=2C=1.Cl.C(N=C=NCCCN(C)C)C.[NH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=1.Cl>CN(C=O)C.C(N(CC)CC)C>[N:4]1[NH:3][N:2]=[N:1][C:5]=1[C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=2)=[O:12])=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 9784-Aminobenzoic AcidHCID 181649HOAtHCID 3231684-(2H-Tetrazol-5-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10086633HCID 10086633, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(2H-tetrazol-5-yl)benzoic acid (example 412, 4 mmol) and HOAt (4.2 mmol) in DMF (6 mL) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (4.2 mmol) and the resulting mixture was stirred at room temperature for 1 hour. An aliquot of this HOAt-ester solution (0.45 mL) was mixed with 0.25 mL of a solution of 4-aminobenzoic acid (1.2 mmol in 1 mL DMF). (Anilines as hydrochlorides can also be utilised, a slight excess of triethylamine was added to the hydrochloride suspension in DMF prior to mixing with the HOAt-ester.) The resulting mixture was shaken for 3 days at room temperature. 1N hydrochloric acid (2 mL) was added and the mixture was shaken for 16 hours at room temperature. The solid was isolated by centrifugation (alternatively by filtration or extraction) and was washed with water (3 mL). Drying in vacuo at 40° C. for 2 days afforded the title compound.

Workup

  1. stirring) The resulting mixture was shaken for 3 days at room temperature
  2. stirringthe mixture was shaken for 16 hours at room temperature
  3. customThe solid was isolated by centrifugation (
  4. filtrationalternatively by filtration or extraction) and
  5. washwas washed with water (3 mL)
  6. customDrying in vacuo at 40° C. for 2 days

Sources & evidence

ORD record
ord-926cc616dcb94d2f95f3c5fa3bbb7f18
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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