1-Methylimidazole → Methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate

HRID 1410078Notes

Reaction equation

HRID 1410078 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24](O)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([O:39][CH3:40])=[O:38])=[N:35][CH:36]=1.CN1C=CN=C1.CCN=C=NCCCN(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([C:37]([O:39][CH3:40])=[O:38])=[N:35][CH:36]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12457877Methyl 5-aminopyridine-2-carboxylateHCID 683795141-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid

Product 1

HCID 66549701Methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinateYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (200 mg, 0.48 mmol) and methyl 5-aminopicolinate (73 mg, 0.48 mmol) in dichloromethane (30 mL) were added the solution of 1-methyl-1H-imidazole (158 mg, 1.92 mmol) and EDCI (368 mg, 1.92 mmol) in dichloromethane (10 mL), the reaction mixture was stirred at room temperature for 15 hours, the solvent was removed in vacuo and methanol (6 mL) was added and stirred for 30 minutes, the solid was collected by filtration and washed with methanol to afford methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate (230 mg, 87.1%) as an orange solid. LC-MS: 550 [M+H]+, tR=1.58 min.

Workup

  1. customthe solvent was removed in vacuo and methanol (6 mL)
  2. additionwas added
  3. stirringstirred for 30 minutes
  4. filtrationthe solid was collected by filtration
  5. washwashed with methanol

Sources & evidence

ORD record
ord-57687260d57f42edab20ec1b7ca4edef
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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