1,2-Dichloroethane → 4-(5-bromo-2-chloropyrimidin-4-yl)-N-(1-(4-chlorophenyl)cyclopropyl)morpholine-3-carboxamide

HRID 2169561Notes

Reaction equation

HRID 2169561 reaction equation
[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([OH:17])=O)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:18]([Cl:21])[CH2:19]Cl.[CH:22]1[CH:23]=[CH:24][C:25]2[N:30](O)N=N[C:26]=2[CH:27]=1.[CH:32](N(CC)C(C)C)(C)C>C1COCC1>[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([NH:30][C:25]2([C:24]3[CH:32]=[CH:19][C:18]([Cl:21])=[CH:22][CH:23]=3)[CH2:26][CH2:27]2)=[O:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86670107HCID 86670107, compound

Product 1

HCID 866701104-(5-bromo-2-chloropyrimidin-4-yl)-N-(1-(4-chlorophenyl)cyclopropyl)morpholine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x31 using 4-(5-bromo-2-chloropyrimidin-4-yl)morpholine-3-carboxylic acid (PREPARATION x30, 0.244 g, 0.756 mmol), EDC (0.174 g, 0.908 mmol), HOBt (0.123 g, 0.908 mmol), N,N-diisopropylethylamine (0.138 mL, 0.794 mmol), and 1-(4-chlorophenyl)cyclopropanamine, HCl (0.185 g, 0.908 mmol) in THF (8 mL). ESI-MS m/z [M+H]+ calc'd for C18H17BrCl2N4O2, 470.99; found 471.3.

Sources & evidence

ORD record
ord-57322828f4f0496789077d4327f38a14
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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