Hydrochloric Acid → (R)-2-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetic acid

HRID 2169633Notes

Reaction equation

HRID 2169633 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:19]=[CH:18][C:17]4[N:16]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[CH2:15][C@@H:14]5[CH2:28][O:29][CH2:30][CH2:31][N:13]5[C:12]=4[N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[ClH:32]>>[ClH:32].[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:19]=[CH:18][C:17]4[N:16]([CH2:20][C:21]([OH:23])=[O:22])[CH2:15][C@@H:14]5[CH2:28][O:29][CH2:30][CH2:31][N:13]5[C:12]=4[N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 60197064(R)-tert-butyl 2-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetate

Product 2

HCID 313Hydrochloric AcidHCID 60197062(R)-2-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetic acidYield 113.1%

Conditions

Temperature
70 °C

Procedure

A mixture of (R)-tert-butyl 2-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetate (250 mg, 0.593 mmol), HCl (4M in 1,4-dioxane) (10 mL, 40.0 mmol) and 1 N hydrochloric acid (2 mL, 2 mmol) was stirred at 70° C. for 1 hour. The mixture was subsequently concentrated in vacuo to give an HCl salt of the title compound as a brown solid (245 mg, 103%). 1H NMR (400 MHz, DMSO-d6) δ 3.17-3.74 (m, 5 H), 3.90-4.03 (m, 2 H), 4.06-4.17 (m, 2 H), 4.46 (d, J=18.19 Hz, 1 H), 4.73 (d, J=12.13 Hz, 1 H), 7.00 (br s, 1 H), 7.29 (t, J=7.83 Hz, 1 H), 7.52-7.62 (m, 2 H), 7.69 (d, J=7.83 Hz, 2 H), 11.61 (br s, 1 H), 13.14 (br s, 1 H) 14.22 (br s, 1 H). ESI-MS m/z [M+H]+ calc'd for C19H19N5O3, 366.15; found 366.2.

Workup

  1. concentrationThe mixture was subsequently concentrated in vacuo

Sources & evidence

ORD record
ord-6d953eb160f5401d977b14b9131a238a
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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