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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide

HRID 2382063
Notes
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Reaction equation

HRID 2382063 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([OH:16])=O)=[CH:9][N:8]=1.[CH2:17]([C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][C:29]([F:32])([F:31])[F:30])[CH:26]=2)[N:21]([NH2:33])[CH:20]=1)[CH3:18].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH2:17]([C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][C:29]([F:30])([F:32])[F:31])[CH:26]=2)[N:21]([NH:33][C:14]([C:10]2[C:11]([CH3:13])=[N:12][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:8][CH:9]=2)=[O:16])[CH:20]=1)[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 685555083-ethyl-5-trifluoromethoxy-1H-indol-1-ylamine

Product 1

HCID 592000234-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amideYield 68%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(2-pyridyl)-4-methyl-pyrimidine-5-carboxylic acid (250 mg, 1.1 mmol) and 3-ethyl-5-trifluoromethoxy-indol-1-ylamine (244 mg, 1.0 mmol) in DMF (5 mL) is stirred at 50° C. for 1 h. The mixture is treated with DMTMM (276 mg, 1.0 mmol) and stirred at 50° C. for 1 h. The mixture is diluted with saturated aqueous Na2CO3 (5 mL) and stirred for 10 min. The precipitate is collected by filtration, washed with H2O (50 mL) and heptane (50 mL), and dried in vacuo to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide (300 mg, 68%). MS: 442 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.27 (s, 1H), 8.81 (d, 1H), 8.47 (d, 1H), 8.03 (m, 1H), 7.57 (m, 3H), 7.47 (s, 1H), 7.21 (d, 1H), 2.78 (s, 3H), 2.74 (q, 2H), 1.29 (t, 3H).

Workup

  1. stirringstirred for 10 min
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with H2O (50 mL) and heptane (50 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-60c9eb31b1244e9fba34f74ef7dd95ac
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes