Nitrogen → HCID 11691375, compound

HRID 502643Notes

Reaction equation

HRID 502643 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:36][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)[C:14]=3[C:13]=2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:8][CH:7]=1.N#N.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[O:36][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)[C:14]=3[C:13]=2[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 58603283HCID 58603283, compound

Product 1

HCID 11691375HCID 11691375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(2-(6-(4-(2-methoxyethoxy)phenyl)-5-phenylfuro[2,3-d]pyrimidin-4-ylamino)ethyl)piperazine-1-carboxylate 35 (Prepared in a manner analogous to Steps 1-2 of Example 7; 60 mg, 0.104 mmol) was dissolved in CH2Cl2 (1.5 mL). After purging with N2, TFA (0.37 mL, 4.8 mmol) was added and the mixture was allowed to stir at RT for 4 h. The reaction mixture was concentrated to remove TFA then taken up in CH2Cl2 and washed with saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated. Preparative TLC (SiO2, 20% MeOH in CH2Cl2) afforded the title compound 36. Mass for C27H31N5O3 found: 474 (M+H+).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customto remove TFA
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-534d6792f19e49ca9d4568d73299f2e1
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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