Triethylamine → HCID 178521685, compound

HRID 72557Notes

Reaction equation

HRID 72557 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.[NH:47]1[C:51]([C:52]2[CH:57]=[CH:56][C:55]([C:58]3([NH2:61])[CH2:60][CH2:59]3)=[CH:54][CH:53]=2)=[N:50][N:49]=[N:48]1.C(N(CC)CC)C>CN(C)C=O>[NH:50]1[C:51]([C:52]2[CH:53]=[CH:54][C:55]([C:58]3([NH:61][C:7](=[O:9])[C:6]4[CH:10]=[C:2]([Cl:1])[CH:3]=[N:4][C:5]=4[N:11]4[CH2:14][CH:13]([O:15][C:16]5[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=5)[CH2:12]4)[CH2:59][CH2:60]3)=[CH:56][CH:57]=2)=[N:47][N:48]=[N:49]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 679588615-Chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinic acidHCID 178479016HCID 178479016, compound

Product 1

HCID 178521685HCID 178521685, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To mixture of 5-chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinic acid (D77) (60 mg, 0.186 mmol) in dry dimethylformamide (1 ml), 1-Hydroxybenzotriazole hydrate (28.5 mg, 0.189 mmol), 1-Ethyl-3-[3-dimethylaminopropyl]carbodiimide Hydrochloride (53.5 mg, 0.279 mmol) were added followed by the addition of a solution of 1-(4-(1H-tetrazol-5-yl)phenyl)cyclopropanamine hydrochloride (D17) (44.2 mg, 0.186 mmol) and triethylamine (26 μl, 0.189 mmol) in dry dimethylformamide. The mixture was stirred for 1 h at room temperature. The solvent was evaporated in vacuo and the resulting residue was taken in NH4Cl sat. sol (10 ml) and extracted with ethylacetate (2×10 ml). Collected organics after solvent evaporation afforded a residue that was washed with methanol (2 ml) to afford the title compound (E82) (30.8 mg)

Workup

  1. additionwere added
  2. customThe solvent was evaporated in vacuo
  3. extractionextracted with ethylacetate (2×10 ml)
  4. customCollected organics after solvent evaporation
  5. customafforded a residue that
  6. washwas washed with methanol (2 ml)

Sources & evidence

ORD record
ord-4068b9ec056449979cf688e7a8c99105
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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