tert-butyl N-(4-aminobutyl)carbamate → HCID 86595104, compound

HRID 859112Notes

Reaction equation

HRID 859112 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])=[O:16])([CH3:13])([CH3:12])[CH3:11].[CH2:23]([O:25][C:26]([C:28]1[CH:29]=[C:30]([NH:34][C:35]2[N:40]=[C:39]([C:41]3[S:45][C:44](Cl)=[N:43][C:42]=3[C:47]([F:50])([F:49])[F:48])[CH:38]=[CH:37][N:36]=2)[CH:31]=[CH:32][CH:33]=1)=[O:27])[CH3:24]>C(#N)C>[CH2:23]([O:25][C:26]([C:28]1[CH:29]=[C:30]([NH:34][C:35]2[N:40]=[C:39]([C:41]3[S:45][C:44]([NH:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])=[N:43][C:42]=3[C:47]([F:49])([F:50])[F:48])[CH:38]=[CH:37][N:36]=2)[CH:31]=[CH:32][CH:33]=1)=[O:27])[CH3:24]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 81531DiisopropylethylamineHCID 69630855HCID 69630855, compound

Product 1

HCID 86595104HCID 86595104, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diisopropylethylamine (0.1 mL, 0.6 mmol) and 4-t-butoxycarbonylamino-butylamine (25 mg, 1.4 mmol) are added to a solution of N-[3-ethoxycarbonyl-phenyl]-4-[2-chloro-4-trifluoromethyl-5-thiazolyl]-2-pyrimidineamine (52 mg, 0.12 mmol) in 50 mL anhydrous acetonitrile. The mixture is then heated to reflux overnight. The reaction is stopped, cooled to room temperature and concentrated. Water (30 mL) is added and the reaction mixture is extracted with ethyl acetate (3×100 mL). The combined organic layers are dried over MgSO4, filtered and concentrated. The residue is used in the next step without further purification; ESI-MS (m/z): 567.2 (M++H).

Workup

  1. temperatureThe mixture is then heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additionWater (30 mL) is added
  5. extractionthe reaction mixture is extracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic layers are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is used in the next step without further purification

Sources & evidence

ORD record
ord-ad043861f79b425bac8734e650daf8f5
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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