Trifluoroacetic acid → HCID 178464711, compound

HRID 709861Notes

Reaction equation

HRID 709861 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 acid2×HCID 178464724HCID 178464724, compoundHCID 178471901HCID 178471901, compound

Product 1

HCID 178464711HCID 178464711, compoundYield 49%

Procedure

2-Amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-propan-1-ol was synthesized as per 2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-quinolin-2-yl]-propan-1-ol (Example 18) in 49% yield (TFA salt) using 2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-propionic acid ethyl ester as starting material (TFA salt). MS: m/z=425.20 [M+H]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.70 (d, J=8.8 Hz, 1H), 8.15 (d, J=9.5 Hz, 1H), 7.62 (d, J=9.5 Hz, 1H), 7.50 (d, J=9.3 Hz, 1H), 4.33-4.45 (m, 1H), 4.08-4.25 (m, 2H), 2.15-2.27 (m, 2H), 1.85-1.98 (m, 2H), 1.78 (s, 3H), 1.48-1.64 (m, 2H), 1.04-1.24 (m, 3H), 0.90 (s, 9H).

Sources & evidence

ORD record
ord-2ae7167bcbfe410f8742fd35cd46dd3c
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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