N-{2-amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridin-3-yl}butanamide → HCID 178439847, compound

HRID 241101Notes

Reaction equation

[NH2:1][C:2]1[C:7]([NH:8][C:9](=O)[CH2:10][CH2:11][CH3:12])=[CH:6][C:5]([C:14]2[CH:15]=[CH:16][C:17]3[O:23][CH2:22][CH2:21][N:20]([C:24]4[C:33]5[CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH2:29][C:28]=5[N:27]=[CH:26][N:25]=4)[CH2:19][C:18]=3[CH:36]=2)=[CH:4][N:3]=1>C(O)(=O)C>[CH3:35][C:31]1([CH3:34])[CH2:30][CH2:29][C:28]2[N:27]=[CH:26][N:25]=[C:24]([N:20]3[CH2:19][C:18]4[CH:36]=[C:14]([C:5]5[CH:6]=[C:7]6[N:8]=[C:9]([CH2:10][CH2:11][CH3:12])[NH:1][C:2]6=[N:3][CH:4]=5)[CH:15]=[CH:16][C:17]=4[O:23][CH2:22][CH2:21]3)[C:33]=2[CH2:32]1

Participants

Conditions

Temperature: 120 °C

Procedure

N-{2-amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridin-3-yl}butanamide (50 mg) was dissolved in acetic acid (0.2 mL) and heated in a microwave oven at 150 watts, 120° C. for 30 minutes. The reaction mixture was concentrated, dissolved in methanol (2 mL) and purified by preparative reverse phase HPLC (0.1% aqueous ammonium acetate-acetonitrile) to give 4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(2-propyl-3H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (12 mg, 32% yield), 1H NMR (400 MHz, Methanol-d4): 8.51 (br, 1H), 8.37 (s, 1H), 8.06 (s, 1H), 7.61 (s, 1H), 7.51 (d, 1H), 7.10 (d, 1H), 4.74 (s, 2H), 4.36 (m, 2H), 3.96 (m, 2H), 2.94 (t, 2H), 2.77 (t, 2H), 2.48 (s, 2H), 1.89 (m, 2H), 1.66 (t, 2H), 1.01 (t, 3H), 0.81 (s, 6H); MS (EI) for C28H32N6O: 469 (MH+).

Workup

concentrationThe reaction mixture was concentrated
dissolutiondissolved in methanol (2 mL)
custompurified by preparative reverse phase HPLC (0.1% aqueous ammonium acetate-acetonitrile)

Sources & evidence

ORD record: ord-8ac0b31bc64d490c8946c69b9a1af171
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

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