Bicarbonate Ion → HCID 58223382, compound

HRID 41283Notes

Reaction equation

HRID 41283 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:29][C:30]2(O)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:6]2[C:7]([O:27][CH3:28])=[N:8][N:9]3[C:13]([C:14]4[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH2:22][O:23][CH3:24])=[CH:16][C:15]=4[O:25][CH3:26])=[CH:12][S:11][C:10]=23)[CH2:3][CH2:2]1.C(N(S(F)(F)[F:43])CC)C.C(=O)([O-])O>ClCCl>[CH:1]1([CH2:4][N:5]([C:6]2[C:7]([O:27][CH3:28])=[N:8][N:9]3[C:13]([C:14]4[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH2:22][O:23][CH3:24])=[CH:16][C:15]=4[O:25][CH3:26])=[CH:12][S:11][C:10]=23)[CH2:29][C:30]2([F:43])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH2:3][CH2:2]1.[CH:1]1([CH2:4][N:5]([CH2:29][C:30]2[CH2:35][CH2:34][O:33][CH2:32][CH:31]=2)[C:6]2[C:7]([O:27][CH3:28])=[N:8][N:9]3[C:13]([C:14]4[C:15]([O:25][CH3:26])=[CH:16][C:17]([CH2:22][O:23][CH3:24])=[CH:18][C:19]=4[O:20][CH3:21])=[CH:12][S:11][C:10]=23)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 123472(Diethylamino)sulfur trifluorideHCID 58223481HCID 58223481, compound

Product 2

HCID 58223382HCID 58223382, compoundHCID 58223478HCID 58223478, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (4 mL) solution of 4-({cyclopropylmethyl-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-amino}-methyl)-tetrahydro-pyran-4-ol (64.5 mg, 0.124 mmol) was added dropwise diethylaminosulfur trifluoride (DAST) (24.6 μL, 0.186 mmol), and the mixture was stirred for five minutes. After the reaction was completed, a saturated aqueous solution of hydrogencarbonate was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by HPLC to obtain cyclopropylmethyl-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-(4-fluoro-tetrahydro-pyran-4-ylmethyl)-amine (8.9 mg, 0.017 mmol) and cyclopropylmethyl-(3,6-dihydro-2H-pyran-4-ylmethyl)-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-amine (1.3 mg, 0.003 mmol).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe mixture was filtered
  4. distillationthe solvent in the filtrate was distilled off under reduced pressure
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-3b8e912fac974993a7a6dfc6171e4ffe
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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