Water → HCID 86670900, compound

HRID 1521831Notes

Reaction equation

HRID 1521831 reaction equation
C(OC([NH:8][C:9]1[S:10][C:11]2[S:17](=[O:19])(=[O:18])[CH2:16][C:15]3[C:20]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:21][N:22]([CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:14]=3[C:12]=2[N:13]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[NH2:8][C:9]1[S:10][C:11]2[S:17](=[O:19])(=[O:18])[CH2:16][C:15]3[C:20]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:21][N:22]([CH:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[C:14]=3[C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86670901HCID 86670901, compound

Product 1

HCID 86670900HCID 86670900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a fine suspension of ethyl 7-[(tert-butoxycarbonyl)amino]-1-(tetrahydro-2H-pyran-4-yl)-1,4-dihydropyrazolo[3′,4′:4,5]thiopyrano[3,2-d][1,3]thiazole-3-carboxylate 5,5-dioxide (182 mg; 0.37 mmol; 1.00 eq.) in DCM (540 μl) is added TFA (180 μl; 2.34 mmol; 6.40 eq.). The mixture is stirred at rt overnight after which water is added to the reaction mixture. The precipitate is washed with water then dried under vacuum to afford the title compound as an off-white powder. 1H NMR (DMSO) δ 8.34 (bs, 2H), 5.61-5.43 (m, 1H), 4.91 (s, 2H), 4.33 (q, J=7.1 Hz, 2H), 4.12-3.93 (m, 2H), 3.52-3.35 (m, 2H), 3.20-1.87 (m, 4H), 1.33 (t, J=7.1 Hz, 3H). HPLC (max plot) 95.1%; Rt 2.28 min. MS (ESI+): 398.7.

Workup

  1. additionis added to the reaction mixture
  2. washThe precipitate is washed with water
  3. customthen dried under vacuum

Sources & evidence

ORD record
ord-ca65454628a84583be0087764be7424e
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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