Ammonia → HCID 74221397, compound

HRID 928858Notes

Reaction equation

C(O[C@@:5]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([O:30][CH3:31])[C:24]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1)=[C:23]2[Cl:43])([C:12]1[C:13]([CH3:19])=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[C:6]1[N:10]([CH3:11])[N:9]=[N:8][CH:7]=1)(=O)C.[NH3:44].CO>>[Cl:43][C:23]1[C:22]2[C:27](=[CH:28][CH:29]=[C:20]([C:5]([C:12]3[C:13]([CH3:19])=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=3)([C:6]3[N:10]([CH3:11])[N:9]=[N:8][CH:7]=3)[NH2:44])[CH:21]=2)[N:26]=[C:25]([O:30][CH3:31])[C:24]=1[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:37][CH:38]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 86715673HCID 86715673, compound2×

Product 1

HCID 74221397HCID 74221397, compound

Conditions

Temperature: 65 °C

Procedure

A mixture of (S)-(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methyl acetate (646 mg, 1.06 mmol, Intermediate 55) and ammonia in MeOH (3.3 mL, 23 mmol, 7.0 M) in a sealed pressure tube was heated at 65° C. for 18 h, and concentrated in vacuo. The residue was purified by flash column chromatography (40 g silica gel column, 50-100% EtOAc in heptanes, and 5-10% MeOH in CH2Cl2) to give the title compound as an oil. 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=2.02 Hz, 1H), 7.82 (d, J=9.09 Hz, 1H), 7.51 (d, J=8.08 Hz, 2H), 7.37-7.44 (m, 3H), 7.08 (d, J=8.08 Hz, 1H), 7.02 (s, 1H), 6.98 (d, J=8.08 Hz, 1H), 4.34 (s, 2H), 4.09 (s, 3H), 3.94 (s, 3H), 2.56 (s, 3H), 2.30 (s, 3H).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (40 g silica gel column, 50-100% EtOAc in heptanes, and 5-10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-4bfcad4e51b4445c982ffebb37ad1968
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290476B2

Reaction notes

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