Ammonium Hydroxide → HCID 66992589, compound

HRID 557000Notes

Reaction equation

HRID 557000 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:41])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[N:27][C:22]=4[CH2:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([O:32][C:33]([CH3:38])([CH3:37])[C:34]([OH:36])=O)=[CH:31][C:18]3=4)[CH2:10][C:9]2([CH3:40])[CH3:39])=[CH:4][CH:3]=1.Cl.C[N:44](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>CN(C)C=O.C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:41])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4=[CH:24][CH:25]=[CH:26][NH:27][C:22]4=[CH:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([O:32][C:33]([CH3:37])([CH3:38])[C:34]([NH2:44])=[O:36])=[CH:31][C:18]3=4)[CH2:10][C:9]2([CH3:40])[CH3:39])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66758367HCID 66758367, compound

Product 1

HCID 66992589HCID 66992589, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(5-{3-[4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidin-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yloxy)-2-methyl-propionic acid (72 mg, 0.125 mmol) in dimethyl formamide (3 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (48 mg, 0.25 mmol), 1-hydroxybenzotriazole (34 mg, 0.25 mmol), and ammonium hydroxide (170 μL, 0.50 mmol) and triethylamine (100 μL). Stir at rt 48 h. The mixture was poured into chloroform and washed with water. The organic phase was washed with additional water and brine; dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (methylene chloride—90:10 methylene chloride/methanol gradient) to yield the titled compound (22 mg, 31%).

Workup

  1. washwashed with water
  2. washThe organic phase was washed with additional water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography (methylene chloride—90:10 methylene chloride/methanol gradient)

Sources & evidence

ORD record
ord-ee039b0775ec410d833bf5b6270467c4
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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