Acetic Acid → 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoic acid

HRID 44224Notes

Reaction equation

[N:1]1[N:2]=[C:3]([C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.[OH-].[Li+].O.C(O)(=O)C>CO.C(OCC)(=O)C>[N:1]1[N:2]=[C:3]([C:19]2[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of methyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoate (0.5 g, 1.4 mmol) in methanol (20 mL) was added lithium hydroxide (0.16 g, 6.8 mmol) and water (2 mL). The reaction mixture was stirred at 70° C. for 3 days. The reaction pH was acidified by the addition of acetic acid followed by ethyl acetate. The solid was filtered off and washed with water. The solid was re-suspended in ethyl acetate, stirred, filtered off and dried under vacuum. The 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoic acid was obtained as a yellow solid (0.48 g, quantitative). M.p.>300° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.20 (br.s, 1H), 8.83 (br.s, 1H), 8.23 (d, J=4.4 Hz, 1H), 8.05-7.95 (m, 3H), 7.56 (d, J=8.0 Hz, 2H), 7.45 (t, J=4.9 Hz, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.2-7.1 (m, 2H), 6.92 (dd, J=7.6, 4.4 Hz, 1H); LCMS [M+H]: 356.

Workup

filtrationThe solid was filtered off
washwashed with water
stirringstirred
filtrationfiltered off
customdried under vacuum

Sources & evidence

ORD record: ord-ebf8ac7db3f749ef887df238666bbdc2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541407B2

Reaction notes

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