Trifluoroacetic acid → HCID 178464711, compound

HRID 1802079Notes

Reaction equation

C(OC(=O)C(N)(C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2)N=1)C)C.C(O)(C(F)(F)F)=O.C([O:39][C:40](=O)[C:41]([NH2:68])([C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[C:48]([O:57][C@H:58]3[CH2:63][CH2:62][C@H:61]([C:64]([CH3:67])([CH3:66])[CH3:65])[CH2:60][CH2:59]3)[C:49]=2[C:53]([F:56])([F:55])[F:54])[N:44]=1)[CH3:42])C>>[NH2:68][C:41]([C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[C:48]([O:57][C@H:58]3[CH2:59][CH2:60][C@H:61]([C:64]([CH3:67])([CH3:66])[CH3:65])[CH2:62][CH2:63]3)[C:49]=2[C:53]([F:54])([F:55])[F:56])[N:44]=1)([CH3:42])[CH2:40][OH:39]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 178471901HCID 178471901, compound

HCID 178471902HCID 178471902, compound

Product 1

HCID 178464711HCID 178464711, compoundYield 55%

Procedure

2-Amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-propan-1-ol Enantiomer 2 was synthesized as per 2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-quinolin-2-yl]-propan-1-ol (Example 17) in 55% yield as bis-TFA salt using 2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-propionic acid ethyl ester Enantiomer 2 as starting material. MS: m/z=425.30 [M+H]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.68 (d, J=8.5 Hz, 1H), 8.13 (d, J=9.5 Hz, 1H), 7.56 (d, J=9.8 Hz, 1H), 7.51 (d, J=9.0 Hz, 1H), 4.30-4.44 (m, 1H), 4.06-4.24 (m, 2H), 2.12-2.26 (m, 2H), 1.85-1.95 (m, 2H), 1.80 (s, 3H), 1.48-1.62 (m, 2H), 1.03-1.22 (m, 3H), 0.90 (s, 9H).

Sources & evidence

ORD record: ord-24ffc672d4b0466f83bf82091c6fc5b3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349849B2

Reaction notes

Loading…