3-Aminomethyl-4-boc-morpholine → tert-Butyl 3-{[(4-{[bis(2,2,2-trifluoroethyl)amino]carbonyl}-2-nitrophenyl)amino]methyl}morpholine-4-carboxylate

HRID 2217935Notes

Reaction equation

HRID 2217935 reaction equation
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[NH2:24][CH2:25][CH:26]1[CH2:31][O:30][CH2:29][CH2:28][N:27]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>CCO>[F:11][C:10]([F:13])([F:12])[CH2:9][N:8]([CH2:14][C:15]([F:17])([F:18])[F:16])[C:6]([C:5]1[CH:19]=[CH:20][C:2]([NH:24][CH2:25][CH:26]2[CH2:31][O:30][CH2:29][CH2:28][N:27]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=1)=[O:7]

Participants

4

Reactant 2

HCID 441823253-Aminomethyl-4-boc-morpholineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 58874473tert-Butyl 3-{[(4-{[bis(2,2,2-trifluoroethyl)amino]carbonyl}-2-nitrophenyl)amino]methyl}morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the general procedure for Intermediate 2 using 4-fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (213 mg, 0.612 mmol) and tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (160 mg, 0.734 mmol) in 10 mL of EtOH containing TEA (0.130 mL, 0.918 mmol). The product was purified by flash chromatography on silica gel using 2:1/hexanes:EtOAc as eluent. Yield: 304 mg (91%); 1H NMR (400 MHz, CHLOROFORM-D) δ 1.49 (s, 9H), 3.17 (m, 1H), 3.52 (m, 1H), 3.64 (m, 3H), 3.92 (m, 2H), 4.25 (q, J=8.20 Hz, 6H), 7.57 (d, J=8.59 Hz, 1H), 8.30 (d, J=1.95 Hz, 1H), 8.48 (m, 1H); MS (ESI) 544.75 (MH+).

Workup

  1. customThe product was purified by flash chromatography on silica gel using 2:1/hexanes

Sources & evidence

ORD record
ord-e6638f2d24954902bedae6b8409e16e2
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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