1,2-Dichloroethane → HCID 86670109, compound

HRID 1631722Notes

Reaction equation

HRID 1631722 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.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[C:39]1([CH3:48])[CH:44]=[CH:43][C:42]([C@@H:45]([NH2:47])[CH3:46])=[CH:41][CH:40]=1>CN(C=O)C>[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([NH:47][C@H:45]([C:42]2[CH:43]=[CH:44][C:39]([CH3:48])=[CH:40][CH:41]=2)[CH3:46])=[O:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 7015759(S)-1-(p-tolyl)ethanamineHCID 86670107HCID 86670107, compound

Product 1

HCID 86670109HCID 86670109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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, 1 g, 3.10 mmol), EDC (0.892 g, 4.65 mmol), HOBt (0.712 g, 4.65 mmol), triethylamine (1.296 mL, 9.30 mmol) and (S)-1-p-tolylethanamine (0.629 g, 4.65 mmol) in DMF (15 mL). 1H NMR (400 MHz, DMSO-d6) δ 1.37 (dd, J=6.95, 3.66 Hz, 3H), 2.27 (s, 3H), 3.55 (d, J=9.35 Hz, 2H), 3.66-3.77 (m, 1H), 3.82-3.92 (m, 1H), 4.21-4.39 (m, 2H), 4.83-5.01 (m, 2H), 7.12 (d, J=7.83 Hz, 2H), 7.16-7.28 (m, 2H), 8.45 (d, J=10.86 Hz, 2H). ESI-MS m/z [M+H]+ calc'd for C18H20BrClN4O2, 439.05. found 439.2.

Sources & evidence

ORD record
ord-14a9e163f6084820887130893b194f8c
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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