HCID 90159395, compound → HCID 74767063, compound

HRID 629808Notes

Reaction equation

HRID 629808 reaction equation
C(O[C:4](=[O:43])[CH2:5][NH:6][C:7]1[C:12]([NH2:13])=[C:11]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[N:21]([CH2:36][CH2:37][N:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=4)[N:24]=3)[CH2:16][CH2:15]2)[N:10]=[CH:9][N:8]=1)C>CCO>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[N:24]=[C:20]([CH:17]3[CH2:18][CH2:19][N:14]([C:11]4[C:12]5[NH:13][C:4](=[O:43])[CH2:5][NH:6][C:7]=5[N:8]=[CH:9][N:10]=4)[CH2:15][CH2:16]3)[N:21]([CH2:36][CH2:37][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH:22]=2)=[CH:26][C:27]=1[C:32]([F:35])([F:34])[F:33]

Participants

3

Reactant 1

HCID 90159395HCID 90159395, compound

Product 1

HCID 74767063HCID 74767063, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of (5-amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamino)-acetic acid ethyl ester (80.00 mg; 0.13 mmol; 1.00 eq.) in EtOH (10 mL) was refluxed for 15 hours. After reverse phase HPLC purification, 4-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-7,8-dihydro-5H-pteridin-6-one (55 mg, 74% yield) was obtained; LC/MS: 559 (M+H);

Workup

  1. customAfter reverse phase HPLC purification

Sources & evidence

ORD record
ord-5c77102fecb54b0793cef02b49d897fe
Source dataset
uspto-grants-2016_04
Patent number
US09315517B2

Reaction notes

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