Triethylamine → HCID 178483077, compound

HRID 1984934Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:15]([O:22][C:23](=[O:34])[NH:24][CH2:25][CH2:26][C@H:27]1[CH2:32][CH2:31][C@@H:30]([NH2:33])[CH2:29][CH2:28]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CC(O)C>[CH2:15]([O:22][C:23](=[O:34])[NH:24][CH2:25][CH2:26][C@H:27]1[CH2:28][CH2:29][C@@H:30]([NH:33][C:2]2[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:31][CH2:32]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of (2-chloro-quinazolin-4-yl)-dimethyl-amine obtained in step B of example 1 (2.45 g, 10.2 mmol) and cis-[2-(4-amino-cyclohexyl)-ethyl]-carbamic acid benzyl ester (3.3 g, 10.2 mmol) and triethylamine (1.65 mL, 10.2 mmol) in 2-propanol (15 mL) was heated at 170° C. for 45 min using a Smith Microwave Synthesizer. The mixture was concentrated and the residue was purified by column chromatography (silica gel, CH2Cl2 to 10% 2 M NH3/MeOH in CH2Cl2) to give cis{2-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexyl]-ethyl}-carbamic acid benzyl ester (4.48 g, 85%) as a yellow oil.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by column chromatography (silica gel, CH2Cl2 to 10% 2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-7bde555a804d4fd1b074de045c365189
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544690B2

Reaction notes

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