5-Chloro-2-picolinic acid → (R)-5-chloro-N-(3-(6,6-difluoro-5,7,7-trimethyl-3-thioxo-[1,4]oxazepan-5-yl)-4-fluorophenyl)picolinamide

HRID 1186155Notes

Reaction equation

HRID 1186155 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]2([CH3:20])[C:14]([F:16])([F:15])[C:13]([CH3:18])([CH3:17])[O:12][CH2:11][C:10](=[S:19])[NH:9]2)[CH:7]=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:29](O)=[O:30])=[N:27][CH:28]=1>>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]3([CH3:20])[C:14]([F:16])([F:15])[C:13]([CH3:17])([CH3:18])[O:12][CH2:11][C:10](=[S:19])[NH:9]3)[CH:7]=2)=[O:30])=[N:27][CH:28]=1

Participants

3

Reactant 2

HCID 27628725-Chloro-2-picolinic acidHCID 58563112(R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione

Product 1

HCID 86660415(R)-5-chloro-N-(3-(6,6-difluoro-5,7,7-trimethyl-3-thioxo-[1,4]oxazepan-5-yl)-4-fluorophenyl)picolinamide

Procedure

The compound was prepared in an analogous manner as described for intermediate B14A from (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepane-3-thione (intermediate A17B) (150 mg, 0.47 mmol) and commercially available 5-chloro-pyridine-2-carboxylic acid [CAS No. 86873-60-1] (111 mg, 0.71 mmol). The compound was obtained as a yellow foam (330 mg, 99%, 65% purity). MS (ISP): m/z=460.4 [(M+H)+] and 462.1 [(M+2+H)+].

Workup

  1. customThe compound was prepared in an analogous manner
  2. customThe compound was obtained as a yellow foam (330 mg, 99%, 65% purity)

Sources & evidence

ORD record
ord-619bd378caa24ffa9a7e43944fb04ec8
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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