1,1'-Carbonyldiimidazole → HCID 69941210, compound

HRID 1935336Notes

Reaction equation

[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:20]1C=CN=C1)=O.N[C@@H:31]1[CH2:36][CH2:35][C:34]2[C:37]([N:44]3[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]3)=[CH:38][CH:39]=[C:40]([C:41](=[O:43])[NH2:42])[C:33]=2[O:32]1>CN(C)C=O>[C:41]([C:40]1[C:33]2[O:32][CH2:31][C@@H:36]([NH:20][C:13](=[O:15])[C:12]3[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:17][CH:16]=3)[CH2:35][C:34]=2[C:37]([N:44]2[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]2)=[CH:38][CH:39]=1)(=[O:43])[NH2:42]

Participants

Conditions

Temperature: 75 °C

Procedure

4—Benzoylbenzoic acid (95 mg, 0.42 mmol) and 1,1′-carbonyldiimidazole (71 mg, 0.44 mmol) were dissolved in N,N-dimethylformamide (2 mL) and stirred at 75° C. for 1 h. The reaction mixture was cooled to room temperature and a solution of (S)-2-amino-8-carbamoyl-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (120 mg, 0.40 mmol) in N,N-dimethylformamide (5 mL) was added. The reaction mixture was stirred at room temperature for 4 days and the solvent was evaporated in vacuo giving 290 mg of a crude product. Purification by preparative TLC on silica using chloroform/ethanol (saturated with ammonia) (15:1) as the eluent afforded 75 mg (38% yield) of the title compound: mp 259° C. (dec); EIMS (70eV) m/z (relative intensity) 498 (38, M+); [α]21D−3° (c 0.1, chloroform).

Workup

temperatureThe reaction mixture was cooled to room temperature
stirringThe reaction mixture was stirred at room temperature for 4 days
customthe solvent was evaporated in vacuo
customgiving 290 mg of a crude product
customPurification by preparative TLC on silica

Sources & evidence

ORD record: ord-6c4d7bad25e64bb9a02dbc2a5d552545
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06387899B1

Reaction notes

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