2-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate → (2S)-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)butan-2-amine

HRID 241154Notes

Reaction equation

HRID 241154 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.[C@@H:29]([N:33]([CH2:44][C:45]1[N:54]=[C:53](Cl)[C:52]2[CH2:51][C:50]([CH3:57])([CH3:56])[CH2:49][CH2:48][C:47]=2[N:46]=1)C(=O)OCC1C=CC=CC=1)([CH2:31][CH3:32])[CH3:30]>>[CH3:57][C:50]1([CH3:56])[CH2:49][CH2:48][C:47]2[N:46]=[C:45]([CH2:44][NH:33][C@H:29]([CH2:31][CH3:32])[CH3:30])[N:54]=[C:53]([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:52]=2[CH2:51]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 86647845(S)-benzyl sec-butyl((4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)methyl)carbamate

Product 1

HCID 57389903(2S)-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)butan-2-amine

Procedure

Prepared according to the method of example 6 by 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 (S)-benzyl sec-butyl((4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)methyl)carbamate (reagent preparation 17) in step 3 followed by Cbz deprotection. 1H NMR (400 MHz, DMSO-d6) δ 8.61-8.44 (m, 1H), 8.12-7.93 (m, 1H), 7.71 (d, 1H), 7.54 (dd, 1H), 7.03 (d, 1H), 4.67 (s, 2H), 4.35-4.27 (m, 2H), 3.92-3.84 (m, 2H), 3.56 (q, 2H), 2.69 (t, 3H), 2.54 (s, 2H), 2.45 (s, 3H), 2.42-2.30 (m, 1H), 1.59 (t, 2H), 1.27 (dd, 2H), 1.18-1.04 (m, 1H), 0.87 (s, 6H), 0.83 (d, 3H), 0.70 (t, 3H); MS (EI) for C31H39N7O: 526 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f3763a44bc3243429de9bfb0cbc1de12
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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