4-Methylmorpholine → [2-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 480184Notes

Reaction equation

HRID 480184 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH3:22])=[O:7].CN1CCOCC1.[C:35]([O:39][C:40]([NH:42][CH2:43][CH2:44][C:45](O)=[O:46])=[O:41])([CH3:38])([CH3:37])[CH3:36].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[C:35]([O:39][C:40](=[O:41])[NH:42][CH2:43][CH2:44][C:45](=[O:46])[NH:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH3:22])=[O:7])([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114861502-(2-Amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-ethanone

Product 1

HCID 69911989[2-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl esterYield 119.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-ethanone (0.066 g, 0.17 mmol) in methylene chloride (2 mL) at ambient temperature was added N-methylmorpholine (0.025 mL, 0.23 mmol), 3-tert-butoxycarbonylamino-propionic acid (0.044 g, 0.23 mmol) and O-benzotriazole-1-yl-N,N,N′, N′-tetramethyluronium hexafluorophosphate (0.076 g, 0.20 mmol). The resulting solution was stirred at ambient temperature for 60 hours, then concentrated. Radial chromatography (2 mm plate) gave the title compound (0.114 g)

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-efb36d67a4964bf889333755fb739089
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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