Sulfuric Acid → HCID 72202966, compound

HRID 1482936Notes

Reaction equation

HRID 1482936 reaction equation
S(=O)(=O)(O)O.[Si]([O:13][CH2:14][CH2:15][O:16][C:17]1[C:18]([NH:39][C:40]2[C:45]([C:46]#[N:47])=[CH:44][N:43]=[CH:42][CH:41]=2)=[N:19][C:20]([C:23]2[C:24]3[CH2:38][CH2:37][CH2:36][C:25]=3[N:26]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[N:27]=2)=[N:21][CH:22]=1)(C(C)(C)C)(C)C.C(=O)([O-])[OH:49].[Na+]>>[F:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][N:26]1[C:25]2[CH2:36][CH2:37][CH2:38][C:24]=2[C:23]([C:20]2[N:19]=[C:18]([NH:39][C:40]3[C:45]([C:46]([NH2:47])=[O:49])=[CH:44][N:43]=[CH:42][CH:41]=3)[C:17]([O:16][CH2:15][CH2:14][OH:13])=[CH:22][N:21]=2)=[N:27]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 123859023HCID 123859023, compound

Product 1

HCID 72202966HCID 72202966, compound

Procedure

0.23 mL sulfuric acid (4.18 mmol, 25.0 eq.) were added to 98 mg of 4-({5-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]pyrimidin-4-yl}amino)nicotinonitrile 2-3-10 (0.167 mmol, 1.00 eq.). The reaction mixture was stirred at rt over night. Aqueous saturated sodium hydrogen carbonate was added and the suspension was filtered and washed with water. Purification by flash chromatography provided 4.4 mg (0.01 mmol, 5%) of analytically pure target compound.

Workup

  1. filtrationthe suspension was filtered
  2. washwashed with water
  3. customPurification by flash chromatography
  4. customprovided 4.4 mg (0.01 mmol, 5%) of analytically pure target compound

Sources & evidence

ORD record
ord-b54545c1a884412195efb09d8c28667d
Source dataset
uspto-grants-2016_08
Patent number
US09416125B2

Reaction notes

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