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tert-butyl N-(4-methyl-1,3-thiazol-2-yl)carbamate → Tert-butyl 5-(2-(2-cyanopropan-2-yl)pyridin-4-yl)-4-methylthiazol-2-ylcarbamate

HRID 2370376
Notes
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Reaction equation

HRID 2370376 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])[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]>CCOC(C)=O>[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]([C:9]#[N:10])([CH3:12])[CH3:11])[CH:3]=2)=[C:23]([CH3:25])[N:24]=1)([CH3:16])([CH3:15])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 45117839tert-butyl N-(4-methyl-1,3-thiazol-2-yl)carbamateHCID 592937172-(4-Iodopyridin-2-yl)-2-methylpropanenitrile

Product 1

HCID 59293723Tert-butyl 5-(2-(2-cyanopropan-2-yl)pyridin-4-yl)-4-methylthiazol-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

The title compound is prepared in analogy to the procedure described in Step 1.3, but using 2-(4-iodo-pyridin-2-yl)-2-methyl-propionitrile (Step 21.5) and (4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (Step 18.4). The reaction mixture is stirred for 3 h at 100° C. Title compound: ESI-MS: 359.1 [M+H]+; TLC: Rf=0.47 (Hex/EtOAc, 1:1).

Workup

  1. customThe title compound is prepared in analogy to the procedure

Sources & evidence

ORD record
ord-e96cf8cec417436284ae6aff0bd628cd
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08710085B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes