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)-2-fluoroethanamine

HRID 241158Notes

Reaction equation

HRID 241158 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][N:43]([CH2:54][CH2:55][F:56])C(=O)OCC2C=CC=CC=2)[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][CH2:54][CH2:55][F:56])[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 86647848Benzyl (4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)methyl(2-fluoroethyl)carbamate

Product 1

HCID 86647847N-({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)-2-fluoroethanamine

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 benzyl (4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)methyl(2-fluoroethyl)carbamate (reagent preparation 17) in step 3 followed by Cbz deprotection. 1H NMR (400 MHz, DMSO-d6) δ 12.83 (s, 0.5H), 12.55 (s, 0.5H), 8.57 (d, 0.5H), 8.49 (d, 0.5H), 8.09 (d, 0.5H), 7.97 (d, 0.5H), 7.73 (d, 1H), 7.54 (dd, 1H), 7.03 (dd, 1H), 4.68 (s, 2H), 4.45 (t, 1H), 4.38-4.25 (m, 3H), 3.93-3.82 (m, 2H), 3.66 (s, 2H), 2.85-2.65 (m, 4H), 2.57-2.52 (m, 3H), 2.46 (s, 2H), 1.59 (t, 2H), 0.86 (s, 6H); MS (EI) for C29H34FN7O: 516 (MH+).

Sources & evidence

ORD record
ord-8218bb1734f340069fdee84a096a2993
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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