Water → HCID 178423415, compound

HRID 241222Notes

Reaction equation

C(N([CH:7]([CH3:9])[CH3:8])CC)(C)C.Cl.C1(C[N:18]([C:22]2[NH:23][C:24]3[C:25]([N:41]=2)=[N:26][CH:27]=[C:28]([C:30]2[CH:31]=[CH:32][C:33]4[O:39][CH2:38][CH2:37][NH:36][CH2:35][C:34]=4[CH:40]=2)[CH:29]=3)[C:19](=[O:21])[OH:20])C=CC=CC=1.Cl[C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[C:50]([CH3:53])[CH:51]=2)[N:46]=[CH:45][N:44]=1.O>CN1C(=O)CCC1>[C:7]1([CH2:8][O:20][C:19](=[O:21])[NH:18][C:22]2[NH:41][C:25]3=[N:26][CH:27]=[C:28]([C:30]4[CH:31]=[CH:32][C:33]5[O:39][CH2:38][CH2:37][N:36]([C:43]6[C:52]7[C:47](=[CH:48][CH:49]=[C:50]([CH3:53])[CH:51]=7)[N:46]=[CH:45][N:44]=6)[CH2:35][C:34]=5[CH:40]=4)[CH:29]=[C:24]3[N:23]=2)[CH:9]=[CH:28][CH:29]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Diisopropylethylamine (0.23 g, 1.76 mmol) was added to a solution of phenylmethyl[6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate hydrochloride (0.2 g, 0.44 mmol) and 4-chloro-6-methylquinazoline (0.08 g, 0.44 mmol), in NMP (5 ml) at room temperature. The reaction mixture was heated to 90° C. for 30 minutes, and then cooled to room temperature. Water was added and the resulting suspension was stirred overnight. The precipitate was collected by filtration and dried under vacuum to give phenylmethyl{6-[4-(6-methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3H-imidazo[4,5-b]pyridin-2-yl}carbamate (0.215 g, 87% yield). MS (EI) for C32H27N7O3: 558.1 (MH+).

Workup

temperaturecooled to room temperature
filtrationThe precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-ee61ec29bf534e64a573d7f3a80e8fbc
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

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