Trifluoroacetic acid → N-(5-{5-[(2,3-dihydroxypropylamino)sulfonyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 1360868Notes

Reaction equation

HRID 1360868 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][NH:8][S:9]([C:12]2[S:16][C:15]([C:17]3[S:21][C:20]([NH:22][C:23](=[O:25])[CH3:24])=[N:19][C:18]=3[CH3:26])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:4][O:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][NH:8][S:9]([C:12]1[S:16][C:15]([C:17]2[S:21][C:20]([NH:22][C:23](=[O:25])[CH3:24])=[N:19][C:18]=2[CH3:26])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11998434N-[5-(5-[[(2,2-Dimethyl-1,3-dioxolan-4-YL)methyl]aminosulfonyl}-2-thienyl)-4-methyl-1,3-thiazol-2-YL]acetamide

Product 1

HCID 11998548N-(5-{5-[(2,3-dihydroxypropylamino)sulfonyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[5-(5-{[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]aminosulfonyl}-2-thienyl)-4-methyl-1,3-thiazol-2-yl]acetamide (14) (48 mg; 0.11 mmol; 1 eq), is dissolved in DCM (5 ml). Trifluoroacetic acid (0.2 ml) is added and reaction mixture stirred at room temperature for 30 minutes. The solvents are evaporated and the crude product purified directly by preparative HPLC, affording Compound (17) as a white-off solid (7 mg; 16%). M− (ESI): 390.2; M+ (ESI): 392.2. HPLC (method A), Rt: 2.13 min (purity: 83.5%).

Workup

  1. customreaction mixture
  2. customThe solvents are evaporated
  3. customthe crude product purified directly by preparative HPLC

Sources & evidence

ORD record
ord-27ae1fa9cce84176ad644f8376f94461
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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