HCID 59394706, compound → HCID 59394261, compound

HRID 45129Notes

Reaction equation

HRID 45129 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:20][C:21]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([O:32][C:33]4[C:34]5[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][C:35]=5[N:36]=[CH:37][N:38]=4)=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)=[O:22])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)(C(C)(C)C)(C)C>C1COCC1.O.C(O)(=O)C.CCOC(C)=O>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:20][C:21]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([O:32][C:33]4[C:34]5[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][C:35]=5[N:36]=[CH:37][N:38]=4)=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)=[O:22])[CH:13]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:15]=1

Participants

6

Reactant 1

HCID 59394706HCID 59394706, compound

Product 1

HCID 59394261HCID 59394261, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
32 °C

Procedure

To a solution of tert-butyl 4-(1-(3-((tert-butyldimethylsilyloxy)methyl)-5-(trifluoromethyl)phenylcarbamoyl)-1H-indol-5-yloxy)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.252 g, 0.361 mmol) in 6 mL of THF and 14 mL of water, 26 mL of acetic acid is added. The mixture is heated to 32° C. for 5 h at which point the reaction is diluted with EtOAc, washed with water/pyridine, saturated sodium bicarbonate, brine and dried over sodium sulfate, concentrated to give the title compound. MS (ESI) m/z 584.2 (M+1).

Workup

  1. washwashed with water/pyridine, saturated sodium bicarbonate, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d48d28903ff5491caa05fcce694796f3
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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