HCID 178445729, compound → HCID 178445753, compound

HRID 1036488Notes

Reaction equation

N[C@@](C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2C2C=CC(OC(F)(F)F)=CC=2)C=1)(C)CO.[C:38]([C@H:42]1[CH2:47][CH2:46][C@H:45]([O:48][C:49]2[C:50]([C:66]3[CH:67]=[N:68][CH:69]=[N:70][CH:71]=3)=[C:51]3[C:56](=[CH:57][CH:58]=2)[CH:55]=[C:54]([C@:59]2([CH3:65])[CH2:63][O:62]C(=O)[NH:60]2)[CH:53]=[CH:52]3)[CH2:44][CH2:43]1)([CH3:41])([CH3:40])[CH3:39]>>[NH2:60][C@@:59]([C:54]1[CH:53]=[CH:52][C:51]2[C:56](=[CH:57][CH:58]=[C:49]([O:48][C@H:45]3[CH2:44][CH2:43][C@H:42]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:47][CH2:46]3)[C:50]=2[C:66]2[CH:67]=[N:68][CH:69]=[N:70][CH:71]=2)[CH:55]=1)([CH3:65])[CH2:63][OH:62]

Participants

Reactant 2

HCID 178445729HCID 178445729, compound

HCID 178445751HCID 178445751, compound

Product 1

HCID 178445753HCID 178445753, compoundYield 48%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-(pyrimidin-5-yl)naphthalen-2-yl)propan-1-ol was synthesized as per (R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-(trifluoromethoxy)phenyl)naphthalen-2-yl)propan-1-ol (Example 221) in 48% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(pyrimidin-5-yl)naphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z 417.28 [M−16]+. 1H NMR (MeOD) δ: 9.21 (s, 1H), 8.79 (s, 2H), 7.99-8.05 (m, 2H), 7.59 (dd, J=9.0, 2.0 Hz, 1H), 7.52 (d, J=9.3 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 4.26-4.35 (m, 1H), 3.73 (d, J=10.8 Hz, 1H), 3.69 (d, J=10.8 Hz, 1H), 2.08-2.15 (m, 2H), 1.80-1.87 (m, 2H), 1.52 (s, 3H), 1.14-1.23 (m, 4H), 0.96-1.06 (m, 1H), 0.88 (s, 9H)

Sources & evidence

ORD record: ord-d079d84d65bb41b4972347bc2d944c40
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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