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

HRID 1186156Notes

Reaction equation

HRID 1186156 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.[C:22]([C:24]1[CH:25]=[CH:26][C:27]([C:30](O)=[O:31])=[N:28][CH:29]=1)#[N:23]>>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([C:30]([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:31])=[N:28][CH:29]=1)#[N:23]

Participants

3

Reactant 2

HCID 124007345-Cyanopyridine-2-carboxylic acidHCID 58563112(R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione

Product 1

HCID 86660416(R)-5-cyano-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-cyano-pyridine-2-carboxylic acid [CAS No. 53234-55-2] (105 mg, 0.71 mmol). The compound was obtained as a light brown oil (280 mg, 99%, 75% purity). MS (ISP): m/z=449.2 [(M+H)+].

Workup

  1. customThe compound was prepared in an analogous manner
  2. customThe compound was obtained as a light brown oil (280 mg, 99%, 75% purity)

Sources & evidence

ORD record
ord-532ac3b0daba4d2c9bd767d452ebe34f
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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