1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178522671, compound

HRID 1669820Notes

Reaction equation

HRID 1669820 reaction equation
[CH:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=3)[N:10]=[C:9]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.O.[NH2:57][C:58]1[NH:62][N:61]=[N:60][N:59]=1>CN(C=O)C.O>[CH:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH:57][C:58]4[NH:62][N:61]=[N:60][N:59]=4)=[O:19])=[CH:15][CH:14]=3)[N:10]=[C:9]([C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:26][CH:27]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 673350634-({5-Cyclohexyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-yl}methyl)benzoic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 178522671HCID 178522671, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 128 mg product from Step D above, 66.3 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), 46.8 mg 1-hydroxybenzotriazole hydrate (HOBt) in 1 mL DMF was stirred at room temperature for 30 minutes. 5-Aminotetrazole monohydrate (35.7 mg) was added and the mixture stirred for additional 16 hours. Precipitate the product by adding 1 mL water to the reaction mixture. Collect the product by filtration, wash it with 1:1 DMF and water, water, and MeCN, and dry to give the title compound as a white solid. 1H NMR (CD3OD, 500 MHz) δ 7.995 (d, J=8.2 Hz, 2H), 7.86 (d, J=8.6 Hz, 2H), 7.27˜7.29 (m, 4H), 6.58 (s, 1H), 5.52 (s, 2H), 2.59˜2.65 (m, 1H), 1.75˜1.81 (m, 4H), 1.69˜1.73 (m, 1H), 1.39˜1.46 (m, 2H), 1.24˜1.37 (m, 3H). LC-MS: 2.32 min. (M+H=512.3).

Workup

  1. customCollect the product
  2. filtrationby filtration
  3. washwash it with 1:1 DMF and water, water, and MeCN
  4. customdry

Sources & evidence

ORD record
ord-d08392f849c14b09ad6de91b2a3f0ace
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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