Water → 4-{[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-4-phenyl-1H-imidazol-1-yl]methyl}cyclohexanone

HRID 32629Notes

Reaction equation

HRID 32629 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][N:12]3[C:16]([C:17]4[S:18][C:19]5[N:20]=[CH:21][N:22]=[C:23]([NH2:26])[C:24]=5[N:25]=4)=[C:15]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:14]=[CH:13]3)[CH2:7][CH2:6]2)[O:4]CC1.O.C(O)(C(F)(F)F)=O>CC#N>[NH2:26][C:23]1[C:24]2[N:25]=[C:17]([C:16]3[N:12]([CH2:11][CH:8]4[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]4)[CH:13]=[N:14][C:15]=3[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[S:18][C:19]=2[N:20]=[CH:21][N:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 10095197HCID 10095197, compound

Product 1

HCID 100012704-{[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-4-phenyl-1H-imidazol-1-yl]methyl}cyclohexanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[1-(1,4-Dioxaspiro[4,5]dec-8-ylmethyl)-4-phenyl-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 178) (634 mg) was dissolved in MeCN (10 mL) and water (10 mL) and TFA (0.5 mL) was added. After 48 hours at ambient temperature, the title compound was obtained by preparative RPHPLC (eluting with a gradient of water and MeCN containing 0.1% TFA) as a colourless solid (570 mg, 99%);

Sources & evidence

ORD record
ord-3e7f4097845d4d9b8b6e0fd3192ac110
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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