Trifluoroacetate → (2R)-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 241153Notes

Reaction equation

HRID 241153 reaction equation
FC(F)(F)C([O-])=O.[CH3:8][C:9]1[N:10](C(OCC(C)C)=O)[C:11]2[C:12]([N:28]=1)=[N:13][CH:14]=[C:15]([C:17]1[CH:18]=[CH:19][C:20]3[O:26][CH2:25][CH2:24][NH:23][CH2:22][C:21]=3[CH:27]=1)[CH:16]=2.[C@H:36]([N:40]([CH2:51][C:52]1[N:61]=[C:60](Cl)[C:59]2[CH2:58][C:57]([CH3:64])([CH3:63])[CH2:56][CH2:55][C:54]=2[N:53]=1)C(=O)OCC1C=CC=CC=1)([CH2:38][CH3:39])[CH3:37]>>[CH3:64][C:57]1([CH3:63])[CH2:56][CH2:55][C:54]2[N:53]=[C:52]([CH2:51][NH:40][C@@H:36]([CH2:38][CH3:39])[CH3:37])[N:61]=[C:60]([N:23]3[CH2:22][C:21]4[CH:27]=[C:17]([C:15]5[CH:16]=[C:11]6[NH:10][C:9]([CH3:8])=[N:28][C:12]6=[N:13][CH:14]=5)[CH:18]=[CH:19][C:20]=4[O:26][CH2:25][CH2:24]3)[C:59]=2[CH2:58]1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 668204282-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylateHCID 86647844(R)-benzyl sec-butyl((4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)methyl)carbamate

Product 1

HCID 57389822(2R)-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 as a trifluoroacetate salt 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 (R)-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 8.69 (br s, 3H), 8.24 (br s, 1H), 7.80 (s, 1H), 7.62 (d, 1H), 7.09 (d, 1H), 4.79 (s, 2H), 4.43-4.36 (m, 2H), 4.17-4.11 (m, 2H), 4.00-3.94 (m, 2H), 3.15 (br s, 1H), 2.75 (t, 2H), 2.67 (s, 2H), 2.50 (s, 2H, buried), 1.79-1.66 (m, 1H), 1.62 (t, 2H), 1.46-1.33 (m, 1H), 1.17 (d, 3H), 0.89-0.78 (m, 9H); MS (EI) for C31H39N7O: 526 (MH+).

Sources & evidence

ORD record
ord-c36f68c3f38b4692860aca1f20296a56
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…