HCID 178503571, compound → HCID 178518173, compound

HRID 271395Notes

Reaction equation

HRID 271395 reaction equation
[F:1][C@H:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1.FC(C1C=CC=CC=1F)CO[C@H]1CC[C@H](N)CC1.CS[C:39]1[N:44]=[C:43]([OH:45])[N:42]=[C:41]2[NH:46][N:47]=[CH:48][C:40]=12>CC(O)C.O>[F:1][C@H:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:39]2[N:44]=[C:43]([OH:45])[N:42]=[C:41]3[NH:46][N:47]=[CH:48][C:40]=23)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 178503571HCID 178503571, compoundHCID 178511720HCID 178511720, compoundHCID 178511721HCID 178511721, compound

Product 1

HCID 178518173HCID 178518173, compound

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

From trans-4-[(2R)-2-fluoro-2-(2-fluorophenyl)ethoxy]cyclohexanamine, the resolved product of Example 11, Step 8, and 4-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-6-ol [R. K. Robins, J. Am. Chem. Soc. 79, (1957), 6407-15] in refluxing 2-propanol/water for several days: MS (m+1)=390.4; 1H NMR (400 MHz, CDCl3-CD3OD) 8.2 (s, 1H), 8.0 (s, 1H), 7.5 (m, 1H), 7.4 (dd, 1H), 7.2 (t, 1H), 7.1 (t, 1H), 5.85 (dd, JHF=47 Hz, 1H), 4.2 (m, 1H), 3.75 (m, 2H), 3.4 (m, 1H), 2.7 (m, 1H), 2.1 (m, 2H), 1.4 (m, 2H).

Sources & evidence

ORD record
ord-38a9ce50a05f4b479398c7e56b4e19aa
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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