4-Methylmorpholine → HCID 140570811, compound

HRID 2362647Notes

Reaction equation

HRID 2362647 reaction equation
[Cl:1][C:2]1[C:3]([C:15]2[S:19][C:18]([C:20]3([O:24][CH2:25][O:26][CH3:27])[CH2:23][CH2:22][CH2:21]3)=[N:17][CH:16]=2)=[C:4]2[CH:10]=[C:9](/[C:11](=[N:13]/[OH:14])/[NH2:12])[NH:8][C:5]2=[N:6][CH:7]=1.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH2:38][CH:37]([C:41](O)=[O:42])[CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[NH2:12]/[C:11](=[N:13]\[O:14][C:41]([CH:37]1[CH2:38][CH2:39][CH2:40][N:35]([C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[CH2:36]1)=[O:42])/[C:9]1[NH:8][C:5]2=[N:6][CH:7]=[C:2]([Cl:1])[C:3]([C:15]3[S:19][C:18]([C:20]4([O:24][CH2:25][O:26][CH3:27])[CH2:23][CH2:22][CH2:21]4)=[N:17][CH:16]=3)=[C:4]2[CH:10]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 136379487HCID 136379487, compound

Product 1

HCID 140570811HCID 140570811, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 22B (0.09 g, 0.221 mmol), 1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (0.056 g, 0.243 mmol), N-methylmorpholine (0.085 mL, 0.772 mmol), and 1-hydroxybenzotriazole hydrate (0.017 g, 0.110 mmol) in N,N-dimethylformamide (2.5 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.063 g, 0.331 mmol), and the reaction was stirred at ambient temperature for 3 hours. The reaction was treated with water (15 mL), and the resulting suspension was stirred for 10 minutes and filtered. The solid collected was washed with water and dried under vacuum. The crude material was purified by flash chromatography on silica gel, eluting with a gradient of from 0% to 40% ethyl acetate in hexane, to provide the title compound. MS ESI(+) m/z 619.2 [M+H]+.

Workup

  1. stirringthe resulting suspension was stirred for 10 minutes
  2. filtrationfiltered
  3. customThe solid collected
  4. washwas washed with water
  5. customdried under vacuum
  6. customThe crude material was purified by flash chromatography on silica gel
  7. washeluting with a gradient of from 0% to 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ff69d0faf846480e93c59682b5b28caa
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

Loading…