Ethyl Acetate → tert-Butyl 4-(1-(3-((methylsulfonyloxy)methyl)-5-(trifluoromethyl)phenylcarbamoyl)-1H-indol-5-yloxy)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

HRID 453197Notes

Reaction equation

HRID 453197 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][S:11](Cl)(=[O:13])=[O:12].Cl[CH2:16][C:17]1[CH:18]=[C:19]([NH:27][C:28]([N:30]2[C:38]3[C:33](=[CH:34][C:35]([O:39][C:40]4[C:41]5[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][C:42]=5[N:43]=[CH:44][N:45]=4)=[CH:36][CH:37]=3)[CH:32]=[CH:31]2)=[O:29])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1.CC[O:59]C(C)=O>C(Cl)Cl>[CH3:10][S:11]([O:13][CH2:16][C:17]1[CH:18]=[C:19]([NH:27][C:28]([N:30]2[C:38]3[C:33](=[CH:34][C:35]([O:39][C:40]4[C:41]5[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][C:42]=5[N:43]=[CH:44][N:45]=4)=[CH:36][CH:37]=3)[CH:32]=[CH:31]2)=[O:29])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)(=[O:59])=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67539289HCID 67539289, compound

Product 1

HCID 59394300tert-Butyl 4-(1-(3-((methylsulfonyloxy)methyl)-5-(trifluoromethyl)phenylcarbamoyl)-1H-indol-5-yloxy)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(1-(3-(hydroxymethyl)-5-(trifluoromethypphenylcarbamoyl)-1H-indol-5-yloxy)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8 H)-carboxylate (0.211 g, 0.361 mmol) in 6 mL of DCM with DIEA (0.19 mL, 1.08 mmol) at 0° C., methanesulfonyl chloride (0.037 mL, 0.469 mmol) is added and the reaction stirred for 3 h. At that point the reaction is diluted with EtOAc, washed with saturated sodium bicarbonate, brine and the organic layer is dried over sodium sulfate. Concentration provides a mixture of the title compound and tert-butyl 4-(1-(3-(chloromethyl)-5-(trifluoromethyl)phenylcarbamoyl)-1H-indol-5-yloxy)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8 H)-carboxylate (3:7), which is carried on to next step.

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialthe organic layer is dried over sodium sulfate
  3. concentrationConcentration
  4. customprovides

Sources & evidence

ORD record
ord-b04f1c0a14344e65a04e03a45711f5df
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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