Trifluoroacetic acid → Trifluoroacetic acid

HRID 1631772Notes

Reaction equation

HRID 1631772 reaction equation
[N:1]1[C:10]2[N:9]3[CH2:11][CH2:12][O:13][CH2:14][CH:8]3[CH2:7][NH:6][C:5]=2[CH:4]=[N:3][C:2]=1[C:15]1[C:23]2[C:18](=[C:19]([O:24][CH3:25])[CH:20]=[CH:21][CH:22]=2)[N:17](C(OC(C)(C)C)=O)[CH:16]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:18]=1[NH:17][CH:16]=[C:15]2[C:2]1[N:3]=[CH:4][C:5]2[NH:6][CH2:7][CH:8]3[CH2:14][O:13][CH2:12][CH2:11][N:9]3[C:10]=2[N:1]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68195078HCID 68195078, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 60197765HCID 60197765, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A TFA salt of the title compound was prepared in a manner similar to EXAMPLE 8 using tert-butyl 3-(5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)-7-methoxy-1H-indole-1-carboxylate (60 mg, 0.137 mmol) in CH2Cl2 and TFA. 1H NMR (400 MHz, DMSO-d6) δ 2.92-3.05 (m, 1H), 3.27-3.30 (m, 1H), 3.53-3.66 (m, 1H), 3.76-3.90 (m, 1H), 3.91-3.98 (m, 5H), 3.97-4.06 (m, 1H), 4.08-4.18 (m, 1H), 4.68-4.84 (m, 1H), 6.33-6.45 (br s, 1H), 6.79-6.87 (m, 1H), 7.09-7.20 (m, 1H), 7.38-7.46 (m, 1H), 7.80-7.89 (m, 1H), 8.15-8.23 (m, 1H), 12.18-12.29 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C18H19N5O2S, 338.15. found 338.4.

Sources & evidence

ORD record
ord-525bc1e3d4ab477ebf2dd1c26d636e92
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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