[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → 6-[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl][1,3]thiazolo[5,4-b]pyridin-2-amine

HRID 241106Notes

Reaction equation

HRID 241106 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH:11]C(=O)C)[S:8][C:5]2=[N:6][CH:7]=1.[CH3:15][C:16]1([CH3:40])[CH2:25][CH2:24][C:23]2[N:22]=[CH:21][N:20]=[C:19]([N:26]3[CH2:32][C:31]4[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:30]=4[O:29][CH2:28][CH2:27]3)[C:18]=2[CH2:17]1>>[CH3:15][C:16]1([CH3:40])[CH2:25][CH2:24][C:23]2[N:22]=[CH:21][N:20]=[C:19]([N:26]3[CH2:32][C:31]4[CH:33]=[C:34]([C:2]5[CH:3]=[C:4]6[N:10]=[C:9]([NH2:11])[S:8][C:5]6=[N:6][CH:7]=5)[CH:35]=[CH:36][C:30]=4[O:29][CH2:28][CH2:27]3)[C:18]=2[CH2:17]1

Participants

3

Reactant 2

HCID 66820411[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acidHCID 73553785HCID 73553785, compound

Product 1

HCID 595862326-[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl][1,3]thiazolo[5,4-b]pyridin-2-amine

Procedure

Prepared according to the method of example 5 by using N-(6-bromo[1,3]thiazolo[5,4-b]pyridin-2-yl)acetamide (Journal of Heterocyclic Chemistry (2003), 40, 261-268) and [4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid (reagent preparation 23) in step 1. 1H NMR (400 MHz, d6-DMSO): 8.38 (m, 2H), 7.88 (brs, 2H), 7.83 (d, 1H), 7.72 (d, 1H), 7.76 (dd, 1H), 7.05 (d, 1H), 4.63 (s, 2H), 4.33 (m, 2H), 3.83 (m, 2H), 2.72 (m, 2H), 2.46 (s, 2H), 1.61 (m, 2H), 0.83 (s, 6H); MS (EI) for C25H26N6OS: 459 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-eb49d83bc3d24a7bae554b156db39105
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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