Trifluoroacetic acid → HCID 178525673, compound

HRID 539053Notes

Reaction equation

HRID 539053 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[C@H:25]6[CH2:26][CH2:27][CH2:28][C@H:24]6[O:23][C:22]5=[O:29])=[N:17][C:16]=34)=[CH:8][CH:7]=2)=[N:2]1.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31].C([C@H]1COC(=O)N1)(C)C.CC1(C)C(C)(C)OB(C2C=CC(C3N(COCC[Si](C)(C)C)C=CN=3)=CC=2)O1>>[F:33][C:32]([F:35])([F:34])[C:30]([OH:36])=[O:31].[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[C@H:25]6[CH2:26][CH2:27][CH2:28][C@H:24]6[O:23][C:22]5=[O:29])=[N:17][C:16]=34)=[CH:10][CH:11]=2)=[N:2]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 670343202-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazoleHCID 178519207HCID 178519207, compound

Product 1

HCID 178525673HCID 178525673, compound

Procedure

(3aS,6aR)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)hexahydro-2H-cyclopenta[d]oxazol-2-one (45 mg, 60%) as the TFA salt was made according to the method of Example 1, Step 4, substituting (3aS,6aR)-hexahydro-2H-cyclopenta[d]oxazol-2-one for (S)-4-isopropyloxazolidin-2-one and substituting 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole for 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole in Example 1, Step 8. LCMS (APCI+) m/z 388 [M+H]+.

Sources & evidence

ORD record
ord-8ea88c3722ae437ba50ab19e32a8f4c6
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…