Hydrochloric Acid → HCID 178465495, compound

HRID 1802082Notes

Reaction equation

HRID 1802082 reaction equation
NC(C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2)N=1)(C)COP(=O)(O)O.[ClH:31].C(OC(=O)[NH:38][C:39]([C:55]1[CH:64]=[CH:63][C:62]2[C:57](=[CH:58][CH:59]=[C:60]([O:69][C@H:70]3[CH2:75][CH2:74][C@H:73]([C:76]([CH3:79])([CH3:78])[CH3:77])[CH2:72][CH2:71]3)[C:61]=2[C:65]([F:68])([F:67])[F:66])[N:56]=1)([CH3:54])[CH2:40][O:41][P:42]([O:49]C(C)(C)C)([O:44]C(C)(C)C)=[O:43])(C)(C)C>>[NH2:38][C:39]([C:55]1[CH:64]=[CH:63][C:62]2[C:57](=[CH:58][CH:59]=[C:60]([O:69][C@H:70]3[CH2:71][CH2:72][C@H:73]([C:76]([CH3:79])([CH3:78])[CH3:77])[CH2:74][CH2:75]3)[C:61]=2[C:65]([F:68])([F:66])[F:67])[N:56]=1)([CH3:54])[CH2:40][O:41][P:42](=[O:43])([OH:44])[OH:49].[ClH:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 178453569HCID 178453569, compoundHCID 178465497HCID 178465497, compound

Product 2

HCID 313Hydrochloric AcidHCID 178465495HCID 178465495, compoundYield 88%

Procedure

Phosphoric acid mono-{2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-propyl} ester Enantiomer 1 was synthesized as per Phosphoric acid mono-{2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-quinolin-2-yl]-propyl}ester Enantiomer 1 (Example 30) in 88% yield as bis-HCl salt using [1-[6-(trans-4-tert-Butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-2-(di-tert-butoxy-phosphoryloxy)-1-methyl-ethyl]-carbamic acid tert-butyl ester Enantiomer 1 as starting material. (Note that HPLC purification was not necessary and compound was isolated as bis-HCl salt). MS: m/z=505.20 [M+H]+. 1H NMR (400 MHz, METHANOL-d4) δ ppm: 8.67 (d, J=8.5 Hz, 1H), 8.31 (d, J=9.5 Hz, 1H), 7.85 (d, J=9.3 Hz, 1H), 7.79 (d, J=9.3 Hz, 1H), 4.50-4.62 (m, 1H), 4.34-4.42 (m, 1H), 4.26-4.34 (m, 1H), 2.17-2.29 (m, 2H), 1.88-1.98 (m, 2H), 1.80 (s, 3H), 1.45-1.59 (m, 2H), 1.20-1.34 (m, 2H), 1.07-1.19 (m, 1H), 0.93 (s, 9H).

Workup

  1. custom(Note that HPLC purification

Sources & evidence

ORD record
ord-71da47ae4b4941038a0f186705088644
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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