2-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate → N-({6,6-dimethyl-4-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]-5,6,7,8-tetrahydroquinazolin-2-yl}methyl)methanesulfonamide

HRID 241159Notes

Reaction equation

HRID 241159 reaction equation
[CH3:1][C:2]1[N:3](C(OCC(C)C)=O)[C:4]2[C:5]([N:21]=1)=[N:6][CH:7]=[C:8]([C:10]1[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][NH:16][CH2:15][C:14]=3[CH:20]=1)[CH:9]=2.Cl[C:30]1[C:39]2[CH2:38][C:37]([CH3:41])([CH3:40])[CH2:36][CH2:35][C:34]=2[N:33]=[C:32]([CH2:42][NH:43][S:44]([CH3:47])(=[O:46])=[O:45])[N:31]=1>>[CH3:40][C:37]1([CH3:41])[CH2:36][CH2:35][C:34]2[N:33]=[C:32]([CH2:42][NH:43][S:44]([CH3:47])(=[O:46])=[O:45])[N:31]=[C:30]([N:16]3[CH2:15][C:14]4[CH:20]=[C:10]([C:8]5[CH:9]=[C:4]6[NH:3][C:2]([CH3:1])=[N:21][C:5]6=[N:6][CH:7]=5)[CH:11]=[CH:12][C:13]=4[O:19][CH2:18][CH2:17]3)[C:39]=2[CH2:38]1

Participants

3

Reactant 2

HCID 668204282-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylateHCID 86647849N-((4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)methyl)methanesulfonamide

Product 1

HCID 59586465N-({6,6-dimethyl-4-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]-5,6,7,8-tetrahydroquinazolin-2-yl}methyl)methanesulfonamide

Procedure

Prepared by the method of example 6 using 2-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate and N-((4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)methyl)methanesulfonamide (reagent preparation 17) in step 3. 1H NMR (400 MHz, DMSO-d6) δ 8.52 (br s, 1H), 8.05 (br s, 1H), 7.74 (d, 1H), 7.56 (dd, 1H), 7.27 (t, 1H), 7.06 (d, 1H), 4.68 (s, 2H), 4.37-4.31 (m, 2H), 4.12 (d, 2H), 3.93-3.87 (m, 2H), 2.85 (s, 3H), 2.71 (t, 2H), 2.54 (s, 3H), 2.47 (s, 2H), 1.60 (t, 2H), 0.85 (s, 6H); MS (EI) for C28H33N7O3S: 548 (MH+).

Sources & evidence

ORD record
ord-3e462395996547908232c070aefaee5e
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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