1,2-Dichloroethane → 4-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-methoxy-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

HRID 2169569Notes

Reaction equation

HRID 2169569 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.Cl.[CH3:33][O:34][C:35]1[CH:43]=[C:42]2[C:38]([CH2:39][CH2:40][CH:41]2[NH2:44])=[CH:37][CH:36]=1.C(N(CC)CC)C>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:44][CH:41]2[C:42]3[C:38](=[CH:37][CH:36]=[C:35]([O:34][CH3:33])[CH:43]=3)[CH2:39][CH2:40]2)=[O:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 186278216-Methoxy-2,3-dihydro-1H-inden-1-amine--hydrogen chloride (1/1)HCID 86670107HCID 86670107, compound

Product 1

HCID 866701174-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-methoxy-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

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, 500 mg, 1.550 mmol), EDC (446 mg, 2.325 mmol), HOBt (356 mg, 2.325 mmol), 6-methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride (464 mg, 2.325 mmol) and triethylamine (0.324 mL, 2.325 mmol) in DMF (10 mL). 1H NMR (400 MHz, DMSO-d6) δ 1.76-1.94 (m, 1 H), 2.30-2.47 (m, 1 H), 2.62-2.93 (m, 2 H), 3.48-3.65 (m, 2 H), 3.70 (d, J=4.80 Hz, 3 H), 3.87-3.96 (m, 1 H), 4.24-4.43 (m, 2 H), 4.89-5.01 (m, 1 H), 5.26-5.41 (m, 1 H), 6.70-6.82 (m, 2 H), 7.08-7.18 (m, 1 H), 8.45 (s, 2 H). ESI-MS m/z [M+H]+ calc'd for C19H20BrClN4O3, 467.04; found 467.3.

Sources & evidence

ORD record
ord-3b3cf2580be34da6a474065ecb08aae0
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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