3-Amino-1-propanol → HCID 178458277, compound

HRID 2373710Notes

Reaction equation

HRID 2373710 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:23][C:24]([NH:26][C:27](=[NH:33])[N:28]2[CH:32]=[CH:31][CH:30]=N2)=[O:25])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)[S:11][CH:12]=1.NCCC[OH:38].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:23][C:24]([NH:26][C:27]([NH:28][CH2:32][CH2:31][CH2:30][OH:38])=[NH:33])=[O:25])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 140504872HCID 140504872, compound

Product 1

HCID 178458277HCID 178458277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(2-chlorophenyl)-2-(4-propoxyphenyl)thien-3-yl]-N-[imino(1H-pyrazol-1-yl)methyl]acetamide (0.240 g, 0.50 mmol) in CH2Cl2 (5 mL) was added 3-aminopropanol (0.112 g, 0.12 mL, 1.50 mmol) and diisopropyl ethylamine (0.193 g, 0.26 mL, 1.50 mmol). The solution was stirred overnight at RT. The solvent was removed and the product purified by flash chromatography (15:1 CHCl3:MeOH) to yield 2-[4-(2-chlorophenyl)-2-(4-propoxyphenyl)thien-3-yl]-N-[[(3-hydroxypropyl)amino](imino)methyl]acetamide as a white solid. mp 49-50° C.; MS (ES) m/z 486.09 ([M+H]+). MS (ES) m/z 971.26 ([2M+H]+). Anal. Calcd for C25H28ClN3O3S.0.10 C6H14: C, 62.16; H, 5.99; N, 8.49. Found: C, 62.41; H, 5.70; N, 8.45.

Workup

  1. customThe solvent was removed
  2. customthe product purified by flash chromatography (15:1 CHCl3:MeOH)

Sources & evidence

ORD record
ord-7b0eda490c5b40e4ba0f28e145f2d0b1
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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