4-Methylmorpholine → HCID 178456384, compound

HRID 1984027Notes

Reaction equation

HRID 1984027 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([O:18][C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:28]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])[NH:29][NH2:30].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCl>[C:33]([O:32][C:28]([NH:29][NH:30][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([O:18][C@H:15]2[CH2:16][CH2:17][C@H:12]([C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]3)=[O:11])[CH2:13][CH2:14]2)=[CH:27][CH:26]=1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178456385HCID 178456385, compound

Product 1

HCID 178456384HCID 178456384, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 420 mg (0.93 mmol) of trans-4-[4-(4-Isopropyl-piperazine-1-carbonyl)-cyclohexyloxy]-benzoic acid, 156 mg (1.18 mmol) of tert-butyl carbazate, 272 mg (1.42 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 192 mg (1.42 mmol) of 1-hydroxybenzotriazole, and 574 mg (5.67 mmol) of N-methylmorpholine in 10 ml of dichloromethane was stirred for 3 h at room temperature. After evaporation, the mixture was diluted with AcOEt, washed with water and saturated NaHCO3 solution, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1. The combined product fractions were evaporated to dryness to yield 0.46 g (quant.) of the title compound. MS (m/e): 489.4 (MH+).

Workup

  1. customAfter evaporation
  2. additionthe mixture was diluted with AcOEt
  3. washwashed with water and saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1
  7. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-999d78c377814f519fbd5f8c2ffbc570
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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