3-Amino-1-propanol → HCID 178483552, compound

HRID 2402559Notes

Reaction equation

HRID 2402559 reaction equation
[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][CH2:5][NH:6][N:7]=[C:8]([C:10]1[C:19]2[C:18]([C:20]([OH:22])=[O:21])=[CH:17][C:16](Cl)=[C:15]([C:24]([OH:26])=[O:25])[C:14]=2[C:13]([C:27](=[N:29][NH:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[OH:28])=[CH:12][C:11]=1Cl)[OH:9].[NH2:39][CH2:40][CH2:41][CH2:42][OH:43]>>[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][CH2:5][NH:6][N:7]=[C:8]([C:10]1[C:19]2[C:18]([C:20]([OH:22])=[O:21])=[CH:17][C:16]([NH:39][CH2:40][CH2:41][CH2:42][OH:43])=[C:15]([C:24]([OH:26])=[O:25])[C:14]=2[C:13]([C:27](=[N:29][NH:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[OH:28])=[CH:12][C:11]=1[NH:39][CH2:40][CH2:41][CH2:42][OH:43])[OH:9]

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 178483551HCID 178483551, compound

Product 1

HCID 178483552HCID 178483552, compound

Procedure

Compound 7 (45 mg, 0.089 mmol) was suspended in 3-amino-propanol (0.5 ml) in a microwave reaction vessel. The tube was flushed with nitrogen, sealed and treated at 150° C. for 10 min in the microwave. The mixture was then diluted down with water (25 ml), basified with 2M sodium carbonate and extracted with chloroform (5×5 ml). The organics were treated in the usual manner to afford a blue solid. The crude product was purified by HPLC to obtain 9 as a blue solid. Yield 9 (4.13 mg, 0.0071 mmol, 7.9%): 1H NMR (MeOD) δ: 1.98-2.07(m, 8H), 2.61(s, 12H), 2.84(m, 4H), 3.53(t, 4H, J=6.9 Hz), 3.84(t, 4H, J=6.0 Hz), 4.09(t, 4H, J=7.1 Hz), 7.68(s, 2H); 13C NMR (MeOD) δ: 25.98(2×CH2), 33.15(2×CH2), 39.15(2×CH2), 41.29(2×CH2), 44.71(4×CH3), 57.66(2×CH2), 60.63(2×CH2), 102.06(2×C), 118.41(2×CH), 121.52(2×C), 126.06(2×C), 146.49(2×C), 163.80(2×C═O), 166.72(2×C═O); HRMS (ES+) calcd C30H42N6O6 [M+H]+ 583.3239. Found: 583.3260.

Workup

  1. customThe tube was flushed with nitrogen
  2. customsealed
  3. additiontreated at 150° C. for 10 min in the microwave
  4. additionThe mixture was then diluted down with water (25 ml)
  5. extractionextracted with chloroform (5×5 ml)
  6. additionThe organics were treated in the usual manner
  7. customto afford a blue solid
  8. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-edb5dce72ba5469db1ac891ca1fdd61b
Source dataset
uspto-grants-2014_08
Patent number
US08796456B2

Reaction notes

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