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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-[2,2']bipyrimidinyl-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide

HRID 2382064
Notes
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Reaction equation

HRID 2382064 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=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:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([C:11]3[N:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:5][CH:6]=2)=[O:10])[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 616999854-Methyl-2-(pyrimidin-2-yl)pyrimidine-5-carboxylic acidHCID 685555083-ethyl-5-trifluoromethoxy-1H-indol-1-ylamine

Product 1

HCID 592000004-Methyl-[2,2']bipyrimidinyl-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amideYield 29.4%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (250 mg, 1.1 mmol) and 3-ethyl-5-trifluoromethoxy-indol-1-ylamine (244 mg, 1 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-[2,2′]bipyrimidinyl-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide (130 mg, 29%). MS: 443 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.25 (s, 1H), 9.05 (d, 2H), 7.69 (t, 1H), 7.64 (s, 1H), 7.54 (m, 2H), 7.14 (d, 1H), 2.80 (s, 3H), 2.76 (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-b091460bfc514a9ab86dfe4d5bc1d086
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