L-Phenylalanine → HCID 178523190, compound

HRID 478659Notes

Reaction equation

[O:1]=[C:2]1[C:6]2=[CH:7][NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:36][C@H:37]([C:45]([OH:47])=[O:46])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C.O.C(N(CC)CC)C>[O:1]=[C:2]1[C:6]2=[CH:7][NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:36][CH:37]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45]([OH:47])=[O:46])=[O:21])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 75 °C

Procedure

4-(3-Oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoic acid (30 mg, 0.1 mmol) was dissolved in DMF (0.5 ml) and 18 mg (0.1 mmol) of carbonyldiimidazol (90% pure) was added and the mixture stirred for 4 h. Phenylalanine (33 mg, 0.2 mmol) was dissolved in of H2O (0.5 ml) together with triethylamine (0.05 ml) and added to the activated acid. This reaction mixture was heated at 75° C. for 2 h. After cooling it was made acidic and diluted 5×with H2O. The precipitate was filtered and washed with H2O and dried under vacuum. FlashTube chromatography using EtOAc/MeOH(7:3) yielded a small amount of 2-[4-(3-Oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoylamino]-3-phenyl-propionic acid. The material contained approx. 10% of starting material. 1H NMR (400 MHz, DMSO-d6) δ 8.7 (1H, s), 8.31 (2H, d), 8.21 (1H, d), 7.82 (2H, d), 7.70 (1H, d), 7.62 (1H, t), 7.50 (1H, t), 7.2-7.3(4H, m), 7.17 (1H, t), 4.50 (1H, m), 3.1-3.2 (2H,m).

Workup

additionadded to the activated acid
temperatureAfter cooling it
filtrationThe precipitate was filtered
washwashed with H2O
customdried under vacuum

Sources & evidence

ORD record: ord-fe06e92a97554a9d89e36a8a4be25439
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642249B2

Reaction notes

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