Trifluoroacetic acid methylene chloride → HCID 60197764, compound

HRID 1631770Notes

Reaction equation

HRID 1631770 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](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[N:17](C(OC(C)(C)C)=O)[CH:16]=1.C(Cl)Cl.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>>[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37].[CH3:25][O:24][C:20]1[CH:19]=[C:18]2[C:23]([C:15]([C:2]3[N:3]=[CH:4][C:5]4[NH:6][CH2:7][CH:8]5[CH2:14][O:13][CH2:12][CH2:11][N:9]5[C:10]=4[N:1]=3)=[CH:16][NH:17]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68194555HCID 68194555, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 60197764HCID 60197764, compoundYield 35%

Procedure

A solution of tert-Butyl 3-(5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)-6-methoxy-1H-indole-1-carboxylate (97 mg, 0.222 mmol) and CH2Cl2/TFA (1:1, 3 mL) was stirred at room temperature for 30 minutes. The reaction mixture was subsequently concentrated in vacuo and the crude product was purified by LC/MS using a gradient of 20-30% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). The pure fractions were combined and lyophilized to give a TFA salt of the title compound as a pale yellow solid (26 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ 2.92-3.03 (m, 1H), 3.33-3.35 (m, 3H), 3.55-3.68 (m, 1H), 3.80 (s, 3H), 3.82-3.88 (m, 1H), 3.94-4.18 (m, 2H), 4.70-4.81 (m, 1H), 6.33-6.46 (br s, 1H), 6.82-6.93 (m, 1H), 6.97-7.08 (m, 1H), 7.36-7.50 (m, 1H), 8.07-8.22 (m, 2H), 11.77-11.94 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C18H19N5O2S, 338.15. found 338.4.

Workup

  1. concentrationThe reaction mixture was subsequently concentrated in vacuo
  2. customthe crude product was purified by LC/MS

Sources & evidence

ORD record
ord-bc5b1df6fc7e4dbe8bec97f3977210c3
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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