HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

3-Methoxypropylamine → 1,2-Dimethylimidazol-5-yl-2-{4-[N-(2-mesylethyl)sulphamoyl]anilino}pyrimidine

HRID 1064313
Notes
Print preview

Reaction equation

HRID 1064313 reaction equation
COC[CH2:4][CH2:5][NH2:6].[CH3:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26](F)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[N:14]=2)=[CH:11][N:10]=[C:9]1[CH3:30]>CN(C)C1C=CN=CC=1.CN1C(=O)CCC1>[CH3:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:28])(=[O:27])[NH:6][CH2:5][CH2:4][S:26]([CH3:23])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[N:14]=2)=[CH:11][N:10]=[C:9]1[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 16723-MethoxypropylamineHCID 222735054-(1,2-Dimethylimidazol-5-yl)-2-(4-(fluorosulphonyl)anilino)pyrimidine

Product 1

HCID 696657941,2-Dimethylimidazol-5-yl-2-{4-[N-(2-mesylethyl)sulphamoyl]anilino}pyrimidineYield 161.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
100 °C

Procedure

4-Dimethylaminopyridine (3 mg, 0.025 mmol) and 3-methyoxypropylamine (200 μl, 2 mmol) were added to a solution of 4-(1,2-dimethylimidazol-5-yl)-2-(4-(fluorosulphonyl)anilino)pyrimidine (Method 59; 87 mg, 0.25 mmol) in NMP (1 mL) and the mixture heated at 100° C. for 18 hours. The mixture was allowed to cool to ambient temperature and the solvent removed by evaporation. The residue was purified by preparative LCMS (constant flow of 5% v/v (35% NH3 in MeOH) with a gradient of H2O:CH3CN (5:95 increasing in polarity to 95:5) over 7.5 min) to give the title compound (91 mg, 81%) as a solid. NMR 2.38 (s, 3H), 2.97 (s, 3H), 3.11 (m, 2H), 3.21 (m, 2H), 3.95 (s, 3H), 7.20 (d, 1H), 7.61 (s, 1H), 7.75 (m, 3H), 7.95 (d, 2H), 8.43 (d, 1H), 9.95 (s, 1H); m/z 451.

Workup

  1. temperatureto cool to ambient temperature
  2. customthe solvent removed by evaporation
  3. customThe residue was purified by preparative LCMS (constant flow of 5% v/v (35% NH3 in MeOH) with a gradient of H2O:CH3CN (5:95 increasing in polarity to 95:5) over 7.5 min)

Sources & evidence

ORD record
ord-5ba85213a1304ef79839f1ab60ac58a3
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06969714B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes