Triethylamine → HCID 20718807, compound

HRID 1250710Notes

Reaction equation

HRID 1250710 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:14]=2[C:15]#[N:16])[CH2:9][CH2:8]1.C(N(CC)CC)C.[F:29][C:30]1[CH:31]=[C:32]([CH:37]2[C:42]([C:43](O)=[O:44])=[C:41]([CH3:46])[NH:40][C:39](=[O:47])[N:38]2[CH3:48])[CH:33]=[CH:34][C:35]=1[F:36].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.CCOCC>[C:15]([C:14]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:13]=1[CH:10]1[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][CH2:4][NH:3][C:43]([C:42]2[CH:37]([C:32]3[CH:33]=[CH:34][C:35]([F:36])=[C:30]([F:29])[CH:31]=3)[N:38]([CH3:48])[C:39](=[O:47])[NH:40][C:41]=2[CH3:46])=[O:44])[CH2:8][CH2:9]1)#[N:16]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18326576HCID 18326576, compoundHCID 18326593HCID 18326593, compound

Product 1

HCID 20718807HCID 20718807, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

2-[1-(3-Amino-propyl)-piperidin-4yl]-5-fluoro-benzonitrile dihydrochloride (85.0 mg, 0.254 mmol), triethylamine (108 μl, 0.774 mmol), (−)-4-(3,4-difluorophenyl)-3,6-dimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (75.0 mg, 0.266 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide Hydrochloride (50.9 mg, 0.266 mmol), and 1-hydroxybenzotriazole hydrate (35.9 mg, 0.266 mmol) were combined in dimethylformamide (5 ml) and stirred 24 hr at room temperature After removal of the solvent in vacuo, the residue was treated with saturated sodium bicarbonate (aq.) and extracted with ethyl acetate (3X). The extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a crude oil (140 mg). Flash chromatography on silica gel (133/10/1 of methylene chloride/methanol/conc. ammonium hydroxide) gave the product as a white solid from ether ([αD]=−78.4°, c=0.125 MeOH).

Workup

  1. customAfter removal of the solvent in vacuo
  2. additionthe residue was treated with saturated sodium bicarbonate (aq.)
  3. extractionextracted with ethyl acetate (3X)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude oil (140 mg)

Sources & evidence

ORD record
ord-bc3f97620d02465a970be0722f5c9739
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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