tert-butyl N-(4-methyl-1,3-thiazol-2-yl)carbamate → {5-[2-(1-Cyano-cyclopropyl)-pyridin-4-yl]-4-methyl-thiazol-2-yl}-carbamic acid tert-butyl ester

HRID 444868Notes

Reaction equation

HRID 444868 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)[CH:3]=1.[C:13]([O:17][C:18](=[O:26])[NH:19][C:20]1[S:21][CH:22]=[C:23]([CH3:25])[N:24]=1)([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18](=[O:26])[NH:19][C:20]1[S:21][C:22]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]3([C:11]#[N:12])[CH2:10][CH2:9]3)[CH:3]=2)=[C:23]([CH3:25])[N:24]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 45117839tert-butyl N-(4-methyl-1,3-thiazol-2-yl)carbamateHCID 574170931-(4-Bromopyridin-2-yl)cyclopropanecarbonitrile

Product 1

HCID 59293730{5-[2-(1-Cyano-cyclopropyl)-pyridin-4-yl]-4-methyl-thiazol-2-yl}-carbamic acid tert-butyl ester

Conditions

Temperature
100 °C

Procedure

The title compound is prepared in analogy to the procedure described in Step 1.3, but using 1-(4-bromo-pyridin-2-yl)-cyclopropanecarbonitrile (Step 18.3) and (4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (Step 18.4). The reaction mixture is stirred for 2 h at 100° C., quenched by dilution with EtOAc/H2O, and extracted with EtOAc. The crude product is purified by silica gel column chromatography (Hex/EtOAc, 1:1) to afford 122 mg of the title compound as a white solid: ESI-MS: 357.1 [M+H]+; tR=4.86 min (System 1); TLC: Rf=0.29 (Hex/EtOAc, 1:1).

Workup

  1. customThe title compound is prepared in analogy to the procedure
  2. customquenched by dilution with EtOAc/H2O
  3. extractionextracted with EtOAc
  4. customThe crude product is purified by silica gel column chromatography (Hex/EtOAc, 1:1)

Sources & evidence

ORD record
ord-5b9529fce531405fa06815b809a170b7
Source dataset
uspto-grants-2013_07
Patent number
US08476268B2

Reaction notes

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