Trifluoroacetic acid → 3-(7-Amino-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-(2-cyclopropylethyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

HRID 494637Notes

Reaction equation

HRID 494637 reaction equation
[CH:1]1([CH2:4][CH2:5][C:6]2([CH3:38])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[C:8]([C:17]3[NH:22][C:21]4[CH:23]=[CH:24][C:25]([NH:27]C(=O)OC(C)(C)C)=[CH:26][C:20]=4[S:19](=[O:36])(=[O:35])[N:18]=3)[C:7]2=[O:37])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[NH2:27][C:25]1[CH:24]=[CH:23][C:21]2[NH:22][C:17]([C:8]3[C:7](=[O:37])[C:6]([CH2:5][CH2:4][CH:1]4[CH2:3][CH2:2]4)([CH3:38])[C:15]4[C:10]([C:9]=3[OH:16])=[CH:11][CH:12]=[CH:13][CH:14]=4)=[N:18][S:19](=[O:36])(=[O:35])[C:20]=2[CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136337529Tert-butyl 3-[4-(2-cyclopropylethyl)-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-ylcarbamate

Product 1

HCID 1363848543-(7-Amino-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-(2-cyclopropylethyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 157F (1.06 g, 2.00 mmol) in dichloromethane (10 mL) was treated with trifluoroacetic acid (10 mL) at room temperature for 1 hour. After concentrating in. vacuo, the resulting oil was partitioned between ethyl acetate and aqueous NaHCO3, the organic layer was removed and the aqueous layer extracted 3 times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in. vacuo to yield a solid that was used without further purification. 1H NMR (300 MHz, DMSO-d6): δ ppm−0.25 (m, 2H) 0.25 (m, 2H) 0.46 (m, 2H) 0.80 (m, 1H) 1.57 (s, 3H) 2.15 (m, 1H) 2.32 (m, 1H) 6.99 (m, 2H) 7.44 (d, J=8.82 Hz, 1H) 7.54 (m, 1H) 7.77 (d, J=4.04 Hz, 2H) 8.15 (d, J=7.72 Hz, 1H) 13.55 (s, 1H). MS (ESI+) m/z=438 (M+H)+, 455 (M+NH4)+.

Workup

  1. concentrationAfter concentrating in
  2. customvacuo, the resulting oil was partitioned between ethyl acetate and aqueous NaHCO3
  3. customthe organic layer was removed
  4. extractionthe aqueous layer extracted 3 times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in
  8. customvacuo to yield a solid that
  9. customwas used without further purification

Sources & evidence

ORD record
ord-0ec7dd101d4b4b1595aaf1b41a9ba886
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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