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1-Methylimidazole → Methyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoate

HRID 1410083
Notes
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Reaction equation

HRID 1410083 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:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[C:33]([OH:41])[CH:32]=1.CN1C=CN=C1.CCN=C=NCCCN(C)C>ClCCl>[CH3:38][O:37][C:35](=[O:36])[C:34]1[CH:39]=[CH:40][C:31]([NH:30][C:24]([CH:20]2[CH2:21][CH2:22][CH2:23][N:18]([C:16]3[N:17]=[C:12]([NH:11][C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[C:13]4[N:29]=[CH:28][S:27][C:14]=4[N:15]=3)[CH2:19]2)=[O:25])=[CH:32][C:33]=1[OH:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 77787Methyl p-aminosalicylateHCID 683795141-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid

Product 1

HCID 68379217Methyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoate
Yield 102.5%

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 (80 mg, 0.19 mmol) and methyl 4-amino-2-hydroxybenzoate (32 mg, 0.19 mmol) in dichloromethane (15 mL) were added the solution of 1-methyl-1H-imidazole (63 mg, 0.76 mmol) and EDCI (147 mg, 0.76 mmol) in dichloromethane (5 mL), the reaction mixture was stirred at room temperature for 24 hours, the solvent was removed in vacuo, methanol (5 mL) was added, the precipitate was collected by filtration to afford methyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoate (110 mg, crude) which was used directly in the next step without further purification. LC-MS: tR=565 [M+H]+, 1.64 min.

Workup

  1. customthe solvent was removed in vacuo, methanol (5 mL)
  2. additionwas added
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-719be4983bbd47179142aed0e0d454ad
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921383B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes