Trifluoroacetic acid → HCID 178464711, compound

HRID 709862Notes

Reaction equation

HRID 709862 reaction equation
NC(C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2)N=1)(C)CO.C(O)(C(F)(F)F)=O.C([O:36][C:37](=O)[C:38]([NH2:65])([C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[C:45]([O:54][C@H:55]3[CH2:60][CH2:59][C@H:58]([C:61]([CH3:64])([CH3:63])[CH3:62])[CH2:57][CH2:56]3)[C:46]=2[C:50]([F:53])([F:52])[F:51])[N:41]=1)[CH3:39])C>>[NH2:65][C:38]([C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[C:45]([O:54][C@H:55]3[CH2:56][CH2:57][C@H:58]([C:61]([CH3:64])([CH3:63])[CH3:62])[CH2:59][CH2:60]3)[C:46]=2[C:50]([F:51])([F:52])[F:53])[N:41]=1)([CH3:39])[CH2:37][OH:36]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178464724HCID 178464724, compoundHCID 178471901HCID 178471901, compound

Product 1

HCID 178464711HCID 178464711, compoundYield 52%

Procedure

2-Amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-propan-1-ol Enantiomer 1 was synthesized as per 2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-quinolin-2-yl]-propan-1-ol (Example 18) in 52% 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 1 as starting material. MS: m/z=425.30 [M+H]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.68 (d, J=8.8 Hz, 1H), 8.12 (d, J=9.0 Hz, 1H), 7.47-7.60 (m, 2H), 4.31-4.44 (m, 1H), 4.09-4.26 (m, 2H), 2.13-2.25 (m, 2H), 1.85-1.95 (m, 2H), 1.81 (s, 3H), 1.48-1.62 (m, 2H), 1.03-1.22 (m, 3H), 0.90 (s, 9H).

Sources & evidence

ORD record
ord-e250ade8caa949049210942e1d06cf02
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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