Trifluoroacetic acid methylene chloride → HCID 60197874, compound

HRID 1631775Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9](C(OC(C)(C)C)=O)[CH:8]=[C:7]2[C:18]1[N:27]=[CH:26][C:25]2[NH:24][CH2:23][CH:22]3[CH2:28][O:29][CH2:30][CH2:31][N:21]3[C:20]=2[N:19]=1.C(Cl)Cl.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>>[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:18]1[N:27]=[CH:26][C:25]2[NH:24][CH2:23][CH:22]3[CH2:28][O:29][CH2:30][CH2:31][N:21]3[C:20]=2[N:19]=1

Participants

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chloride

HCID 68195420HCID 68195420, compound

Product 2

HCID 6422Trifluoroacetic acid

HCID 60197874HCID 60197874, compoundYield 27%

Conditions

Temperature: 50 °C

Procedure

A mixture of tert-butyl 7-chloro-3-(5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)-1H-indole-1-carboxylate and CH2Cl2/TFA (1:1) was heated to 50° C. and stirred for 2 hours. The reaction mixture was subsequently concentrated in vacuo and the crude product purified by LC/MS using a gradient of 30-40% 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 tan solid (20 mg, 27%). 1H NMR (400 MHz, DMSO-d6) δ 2.98-3.01 (m, 2H), 3.56-3.58 (m, 3H), 3.72-4.25 (m, 3H), 4.65-4.92 (m, 1H), 6.34-6.58 (br s, 1H), 7.12-7.59 (m, 3H), 8.12-8.52 (m, 2H), 12.27-12.56 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C17H16ClN5O, 342.10. found 342.3.

Workup

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

Sources & evidence

ORD record: ord-9d0237acf35c4c4d9f814c6f17de481b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791107B2

Reaction notes

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