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

HRID 1948407Notes

Reaction equation

HRID 1948407 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-bdbd702019c1446fa4520ee7061ef37c
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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