Potassium Bromide → (1S,9S) 9-Acetylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

HRID 2230439Notes

Reaction equation

HRID 2230439 reaction equation
[C:1]([NH:9][C@@H:10]1[C:16](=[O:17])[N:15]2[C@H:18]([C:22]([O:24]C(C)(C)C)=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:29])[CH2:12][CH2:11]1)(=[O:8])[C:2]1C=CC=CC=1.[K+].[Br-]>CO>[C:1]([NH:9][C@@H:10]1[C:16](=[O:17])[N:15]2[C@H:18]([C:22]([OH:24])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:29])[CH2:12][CH2:11]1)(=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 57166602(1S, 9S) t-Butyl 9-benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate

Product 1

HCID 18396547(1S,9S) 9-Acetylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

was prepared from 211e the same method as compound 212e as a white glassy solid (595 mg, 77%): mp >250° C.; [α]D24 −153 (c 0.10, MeOH); IR (KBr) 3280, 2942, 1742, 1697, 1675, 1650, 1616, 1548, 1470, 1443, 1281, 1249, 1202, 1187, 1171; 1H NMR (CD3OD) δ5.35-5.31 (1H, m), 4.81-4.71 (1H, m), 4.61-4.46 (1H, m), 3.59-3.44 (2H, m), 3.11-2.94 (1H, m), 2.58-2.39 (1H, m), 2.36-2.19 (2H, m), 2.11-1.83 (3H, m), 1.99 (3H, s), 1.78-1.56 (2H, m); Anal. Calcd for C12H17N3O5: C, 50.88; H, 6.05; N, 14.83. Found: C, 50.82; H, 6.02; N, 14.58; MS (ES−) 282 (M−1, 100%): Accurate Mass calculated for C12H18N3O5 (MH+): 284.1246. Found: 284.1258.

Sources & evidence

ORD record
ord-b111832adb544e1fa363c6a40a4cc162
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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