Diisopropylethylamine → 5-[4-(6,6-Dimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-2,3-diamine

HRID 241231Notes

Reaction equation

Cl.Cl.[O:3]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:13][C:8]=2[CH2:7][NH:6][CH2:5][CH2:4]1.Cl[C:23]1[C:32]2[CH2:31][C:30]([CH3:34])([CH3:33])[CH:29]=[CH:28][C:27]=2[N:26]=[CH:25][N:24]=1.C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1>[CH3:33][C:30]1([CH3:34])[CH:29]=[CH:28][C:27]2[N:26]=[CH:25][N:24]=[C:23]([N:6]3[CH2:7][C:8]4[CH:13]=[C:12]([C:14]5[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[N:18][CH:19]=5)[CH:11]=[CH:10][C:9]=4[O:3][CH2:4][CH2:5]3)[C:32]=2[CH2:31]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a slurry of 5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridine-2,3-diamine dihydrochloride (0.92 g, 2.8 mmol) and 4-chloro-6,6-dimethyl-5,6-dihydroquinazoline (0.55 g, 2.8 mmol) in NMP was added diisopropylethylamine (2.4 mL, 14 mmol) and the reaction mixture was heated (90° C.) for 12 hours. The resulting dark red solution was loaded directly on to a column of dry silica and elution with MeOH (w/8% NH4OH v/v) in CH2Cl2 (0-5%) provided 5-[4-(6,6-dimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-2,3-diamine (0.86, 74% yield) as a brown solid. MS (EI) for C24H26N6O: 415.1 (MH+).

Workup

washThe resulting dark red solution was loaded directly on to a column of dry silica and elution with MeOH (w/8% NH4OH v/v) in CH2Cl2 (0-5%)

Sources & evidence

ORD record: ord-398c158d28734bfabb7e48aefa46e55a
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

Loading…