Diisopropylethylamine → HCID 59705045, compound

HRID 605866Notes

Reaction equation

HRID 605866 reaction equation
[N+:1]([C:4]1[C:5](SC#N)=[N:6][C:7]([NH:10][C:11]2[CH:16]=[C:15]([O:17][C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:13][C:12]=2[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:8][CH:9]=1)([O-:3])=[O:2].[NH2:33][CH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(N(CC)C(C)C)(C)C>C1COCC1.CCOC(C)=O>[C:25]([O:24][C:23](=[O:29])[NH:22][C:12]1[CH:13]=[CH:14][C:15]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:16][C:11]=1[NH:10][C:7]1[N:6]=[C:5]([NH:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)([CH3:26])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 59704978HCID 59704978, compound

Product 1

HCID 59705045HCID 59705045, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)-4-(trifluoromethoxy)phenylcarbamate (0.94 g, 2.0 mmol) was dissolved in 40 mL anhydrous THF, then added 0.22 g (2.2 mmol) 4-amino-tetrahydropyran, and 0.7 mL (4.0 mmol) N,N-diisopropylethylamine. The mixture was stirred at room temperature under Argon balloon for 3 hrs till HPLC showed the completion of reaction. The orange-red solution was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 1.0 g orange-yellow solid as the crude product.

Workup

  1. customthe completion of reaction
  2. washwashed with brine twice
  3. dry with materialdried over Na2SO4
  4. customSolvents were removed under vacuum

Sources & evidence

ORD record
ord-776e73b4613a4ca8965748007c0aff64
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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