Ethanolamine → HCID 59242062, compound

HRID 1876187Notes

Reaction equation

HRID 1876187 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[CH2:22]([CH2:24][NH2:25])[OH:23].CCN(CC)CC.CO.C(Cl)Cl>C(O)(C)C.C(Cl)Cl>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH3:13])[C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=[C:2]([NH:25][CH2:24][CH2:22][OH:23])[N:11]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 21226129Dichloromethane methanolHCID 59242116HCID 59242116, compound

Product 1

HCID 59242062HCID 59242062, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine 0.150 g (0.5 mmol), ethanolamine 0.2 mL (3.0 mmol) with Et3N 0.2 mL in isopropanol 5 mL was stirred at 100° C. for 48 h. The reaction mixture was diluted with CH2Cl2, and directly charged to gradient column chromatography (MeOH/CH2Cl2, 0% to 20%) to give the title compound. For analytical use, it was further purified with preparative HPLC to give the corresponding TFA salt. 1H NMR (CD3OD, 400 MHz) δ 7.19 (d, J=8.0 Hz, 2H,), 6.98 (d, J=8.0 Hz, 2H), 3.83 (s, 3H), 3.76 (t, J=5.6 Hz, 2H), 3.62 (t, J=5.6 Hz, 2H), 3.50 (s, 3H), 2.59 (t, J=6.5 Hz, 2H), 1.60-1.66 (m, 2H), 1.55-1.58 (m, 2H), 1.41-1.46 (m, 2H); HRMS (ES) m/z calcd for C18H24N4O2 (M+H) 329.1972, found 329.1962.

Sources & evidence

ORD record
ord-3e54ee2c3d464d16a768c7b71526ce27
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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