tert-Butylcyclohexane → HCID 178445796, compound

HRID 1802104Notes

Reaction equation

HRID 1802104 reaction equation
C(C1CCCCC1)(C)(C)C.[C:11]([C@H:15]1[CH2:20][CH2:19][C@H:18]([O:21][C:22]2[C:23](C(F)(F)F)=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[C:27]([C@:32]2([CH3:38])[CH2:36][O:35]C(=O)[NH:33]2)[N:26]=[CH:25]3)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12].OC1C=C2C(=CC=1)N=C([C@]1(C)COC(=O)N1)N=C2.N[C@@](C1N=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2C(F)(F)F)N=1)(C)CO>>[NH2:33][C@@:32]([C:27]1[N:26]=[CH:25][C:24]2[C:29](=[CH:30][CH:31]=[C:22]([O:21][C@H:18]3[CH2:17][CH2:16][C@H:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:20][CH2:19]3)[CH:23]=2)[N:28]=1)([CH3:38])[CH2:36][OH:35]

Participants

5

Reactant 4

HCID 18508tert-ButylcyclohexaneHCID 67408663HCID 67408663, compoundHCID 178445793HCID 178445793, compoundHCID 178445797HCID 178445797, compound

Product 1

HCID 178445796HCID 178445796, compound

Procedure

Coupling of t-butyl cyclohexane to the core was performed similar to that described for (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-iodoquinazolin-2-yl)-4-methyloxazolidin-2-one (Example 60) utilizing (R)-4-(6-hydroxyquinazolin-2-yl)-4-methyloxazolidin-2-one as the starting material. Deprotection was then performed similar to that described for (R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)quinazolin-2-yl)propan-1-ol (Example 61) to give the title compound. 1H NMR (MeOD) δ: 9.37 (s, 1H), 7.92 (d, J=9.3 Hz, 1H), 7.57 (dd, J=9.2, 2.6 Hz, 1H), 7.42 (d, J=2.5 Hz, 1H), 4.34-4.49 (m, 1H), 4.05 (d, J=10.8 Hz, 1H), 3.79 (d, J=10.8 Hz, 1H), 2.29 (d, J=10.8 Hz, 2H), 1.93 (d, J=12.8 Hz, 2H), 1.54 (s, 3H), 1.38-1.51 (m, 2H), 1.21-1.35 (m, 2H), 1.08-1.19 (m, 1H), 0.93 (s, 9H). MS (M+1): 358.20.

Sources & evidence

ORD record
ord-39b2c222bc6d4491b5377a1877725e80
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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