Propylamine → HCID 18772120, compound

HRID 479686Notes

Reaction equation

HRID 479686 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:14]=[C:13]([NH:15][C:16]([NH:18][C:19]3[N:20]=[C:21]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[S:22][CH:23]=3)=[O:17])[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[CH2:30]([NH2:33])[CH2:31][CH3:32].[BH4-].[Na+]>CO>[CH2:30]([NH:33][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:14]=[C:13]([NH:15][C:16]([NH:18][C:19]3[N:20]=[C:21]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[S:22][CH:23]=3)=[O:17])[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1)[CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 4311764Sodium borohydrideHCID 18771820HCID 18771820, compound

Product 1

HCID 18772120HCID 18772120, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of N-[2-(4-pyridinyl)-4-thiazolyl]-N′-2-[6-(piperidon-4-yl)methyl]urea (50 mg, 0.12 mmol, Example 175) in MeOH (10 mL) was added propylamine (0.1 mL, 1.22 mmol). The resulting mixture was heated at 50° C. for 4 h under N2. After the mixture was cooled to RT, NaBH4 (83 mg, 2.20 mmol) was added. The mixture was stirred at RT under N2 for 3 h. Solvent was removed in vacuo and the crude product was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH (90:10) gave the title compound as a white solid. MS m/z: 451.7 (M+H). Calc'd. for C23H29N7OS-451.6.

Workup

  1. temperatureAfter the mixture was cooled to RT
  2. customSolvent was removed in vacuo
  3. customthe crude product was purified by chromatography on silica gel
  4. washElution with CH2Cl2:MeOH (90:10)

Sources & evidence

ORD record
ord-f1ea9ff05ad04008a31f6983d9bd7c96
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

Loading…