1-Hydroxybenzotriazole → HCID 58126888, compound

HRID 1971818Notes

Reaction equation

HRID 1971818 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][N:18]([CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:12]2=[N:11][C:10]=1[C:28]([OH:30])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:32][CH2:33][C:34](=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:35][C:34](=[O:43])[CH2:33][NH:32][C:28]([C:10]2[N:11]=[C:12]3[N:18]([CH2:19][C:20](=[O:27])[N:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)[CH:17]=[CH:16][N:13]3[C:14](=[O:15])[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:30])=[CH:41][CH:40]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 132906742-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1)HCID 58126863HCID 58126863, compound

Product 1

HCID 58126888HCID 58126888, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of example 4 (1.0 g, 2.4 mmol) in THF (10 ml) was added compound 1-amino-3-(4-fluoro-phenyl)-propan-2-one hydrochloride (1.0 g, 4.9 mmol), EDCI.HCl (560 mg, 2.9 mmol), HOBt (400 mg, 2.9 mmol) and TEA (1 g, 9.9 mmol) successively at room temperature. The mixture was stirred overnight, after which saturated sodium bicarbonate was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, and then dried over sodium sulfate. The product was purified by column chromatography (CH2Cl2/MeOH=100/1) to give the desired product (540 mg, 40% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe product was purified by column chromatography (CH2Cl2/MeOH=100/1)

Sources & evidence

ORD record
ord-40c431fefd6c4a8981a9e75ad16390b1
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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