HCID 18516879, compound → HCID 18516995, compound

HRID 1370076Notes

Reaction equation

HRID 1370076 reaction equation
C(OC([NH:8][C:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([C:24]#[N:25])=[CH:22][N:21]=[C:20]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:29][CH:28]=3)[N:19]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=O)(C)(C)C.C(Cl)Cl.FC(C(O)=O)(F)F>>[NH2:8][C:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:23]([C:24]#[N:25])=[CH:22][N:21]=[C:20]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]4)=[CH:31][CH:32]=3)[N:19]=2)=[CH:16][CH:17]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 18516879HCID 18516879, compoundHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 18516995HCID 18516995, compoundYield 77.5%

Procedure

4-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-5-cyano-N-[4-(2-piperidin-1-ylethyl)phenyl]pyrimidine-2-amine (380 mg) was stirred in 50% v/v CH2Cl2-TFA (5 mL) at room temperature for 30 min. The solvent was removed under reduced pressure and the resulting residue was redissolved in CH2Cl2, washed with saturated aqueous NaHCO3, dried (MgSO4) and evaporated to give the title compound (240 mg) as a yellow solid, m.p. 150°. δH (CDCl3) 8.70 (1H, s), 8.01 (2H, d, J 8.0 Hz), 7.73 (2H, d, J 8.0 Hz), 7.55 (2H, d, J 8.0 Hz), 7.22 (2H, d, J 8.0 Hz), 2.84 (2H, m), 2.63 (2H, m), 2.52 (4H, m) and 1.51 (6H, s).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was redissolved in CH2Cl2
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-372563359df743d5899b5f62a947e74f
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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