2-Fluoropyridine-5-carbonyl chloride → HCID 178502374, compound

HRID 1776042Notes

Reaction equation

HRID 1776042 reaction equation
[CH3:1][O:2][C:3](=[O:39])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[NH:17][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[C:31]([Cl:33])[C:30]([NH2:34])=[CH:29][C:28]=3[C:35]([F:38])([F:37])[F:36])=[CH:23][CH:22]=2)[N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].[F:40][C:41]1[CH:46]=[CH:45][C:44]([C:47](Cl)=[O:48])=[CH:43][N:42]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:39])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[NH:17][CH:18]=[C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[C:31]([Cl:33])[C:30]([NH:34][C:47]([C:44]4[CH:43]=[N:42][C:41]([F:40])=[CH:46][CH:45]=4)=[O:48])=[CH:29][C:28]=3[C:35]([F:37])([F:38])[F:36])=[CH:25][CH:26]=2)[N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 146236022-Fluoropyridine-5-carbonyl chlorideHCID 178502373HCID 178502373, compound

Product 1

HCID 178502374HCID 178502374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ((S)-1-{(S)-2-[4-(4′-amino-5′-chloro-2′-trifluoromethyl-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (50 mg, 0.09 mmol; Preparation 52) dissolved in DCM (0.3 mL) was slowly added a solution of 2-fluoropyridine-5-carbonyl chloride (14 mg, 0.091 mmol) dissolved in DCM (0.3 mL). The reaction mixture was stirred at RT for 5 min and concentrated to produce {(S)-1-[(S)-2-(4-{5′-chloro-4′-[(6-fluoro-pyridine-3-carbonyl)-amino]-2′-trifluoromethyl-biphenyl-4-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester as a yellow solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-319075a2621b4032b7cc5cfd0c982b70
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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