1,2-Dichloroethane → HCID 59640537, compound

HRID 2250141Notes

Reaction equation

HRID 2250141 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([NH2:20])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:21]1([CH2:27][C:28](O)=[O:29])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(C(C)C)CC)(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[N:21]1([CH2:27][C:28]([NH:20][C:17]2([C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:16][CH:15]=3)[CH2:18][CH2:19]2)=[O:29])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4389684-Morpholineacetic acidHCID 59640425HCID 59640425, compound

Product 1

HCID 59640537HCID 59640537, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-cyclopropylamine (0.195 g, 0.72 mmol) and morpholin-4-yl-acetic acid (0.125 g, 0.86 mmol) are dissolved in DMF, and diisopropylethylamine added (0.15 mL), followed by EDC (0.165 g, 0.86 mmol) and HOBt (0.116 g, 0.86 mmol). The reaction mixture was stirred overnight at room temperature. The residue is purified by chromatography [SCX-MeOH wash, elute 2M NH3/MeOH; then Biotage 12M SiO2, elute 10% (25/5/1 CHCl3/MeOH/NH4OH)/90% (10% MeOH/CHCl3)] to give the title compound as a yellow oil. HRMS 402.2765 (M+H)+.

Workup

  1. customThe residue is purified by chromatography [SCX-MeOH
  2. washwash
  3. washelute 2M NH3/MeOH
  4. washthen Biotage 12M SiO2, elute 10% (25/5/1 CHCl3/MeOH/NH4OH)/90% (10% MeOH/CHCl3)]

Sources & evidence

ORD record
ord-8cb01932ff8e4256a04d85fd1549fc02
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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