Formic Acid → Azetidin-3-yl(4-chloro-2-methoxy-3-(4-(trifluoromethyl)-benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol

HRID 926632Notes

Reaction equation

HRID 926632 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([C:12]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[C:27]([O:32][CH3:33])[C:26]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)=[C:25]3[Cl:45])([C:14]2[C:15]([CH3:21])=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[OH:13])[CH2:9]1)=O)(C)(C)C.C(O)=O.Cl>CO>[NH:8]1[CH2:11][CH:10]([C:12]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[C:27]([O:32][CH3:33])[C:26]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]([F:42])([F:43])[F:44])=[CH:39][CH:40]=2)=[C:25]3[Cl:45])([C:14]2[C:15]([CH3:21])=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[OH:13])[CH2:9]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 118006162tert-Butyl-3-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(hydroxy)methyl)azetidine-1-carboxylate

Product 1

HCID 118006245Azetidin-3-yl(4-chloro-2-methoxy-3-(4-(trifluoromethyl)-benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask containing tert-butyl 3-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(hydroxy)methyl)azetidine-1-carboxylate (700 mg, 1.09 mmol, Example 125) was added formic acid (10 mL, 265 mmol) at room temperature followed by 6 N aqueous HCl (500 μL). After 45 minutes, MeOH was added (10 mL) and the mixture was stirred for 15 minutes and then concentrated to provide the title compound as a crude product. MS (ESI): mass calcd. Chemical Formula: C29H27ClF3N3O2; Exact Mass: 541.2. m/z found 541.9 [M+H]+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-c80018b2a90d44cf859bd7eb73ddb262
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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