Water → HCID 178518773, compound

HRID 882803Notes

Reaction equation

HRID 882803 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[NH:27][C:26]3[C:28]4[C:22]([C:23](=[O:29])[NH:24][N:25]=3)=[CH:21][CH:20]=[CH:19][C:18]=4[N:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[N:11]1([CH2:15][C:16]2[NH:27][C:26]3[C:28]4[C:22]([C:23](=[O:29])[NH:24][N:25]=3)=[CH:21][CH:20]=[CH:19][C:18]=4[N:17]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 178452096HCID 178452096, compound2×

Product 1

HCID 178518773HCID 178518773, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized from compound 24. To a solution of 24 (1.5 g, 3.7 mmol) in 30 mL of CH2Cl2 was added 6 mL of TFA while stirring at room temperature. After 30 minutes, the solvents were evaporated and the residue was washed with acetonitrile to afford 1.0 g (90%) of analytically pure white solid. MP: 147-149° C.; MS (ES−): 297; 1H NMR (400 MHz, D2O): 1.96 (m, 2H), 2.82 (t, 2H), 3.01 (t, 2H), 3.28 (t, 4H), 3.53 (s, 2H), 7.22 (d, 1H), 7.47 (d, 1H), 7.61 (t, 1H). Anal. Calcd. for C15H18N6O. 1.1 CF3CO2H. 1.0 H2O.: C, 46.76; H, 4.81; N, 19.02; Found: C, 46.64; H, 4.98; N, 19.02.

Workup

  1. customthe solvents were evaporated
  2. washthe residue was washed with acetonitrile
  3. customto afford 1.0 g (90%) of analytically pure white solid

Sources & evidence

ORD record
ord-6a9c36caa0a74cf5a4419892a1fc26e8
Source dataset
uspto-grants-2012_08
Patent number
US08236802B2

Reaction notes

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