Hydrochloric Acid → HCID 21943195, compound

HRID 968870Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:44]=[CH:43][C:8]2[N:9]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]4[C:25]([C:26]5[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=5)=[CH:24][CH:23]=[C:22]([C:33](=[O:35])[NH2:34])[CH:21]=4)=[CH:14][C:13]=3[F:36])=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[C:33]([C:22]1[CH:21]=[C:20]([CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:10]3[N:9]([CH:37]4[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]4)[C:8]4[CH:43]=[CH:44][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=4[N:11]=3)=[C:13]([F:36])[CH:14]=2)[C:25]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[CH:24][CH:23]=1)(=[O:35])[NH2:34]

Participants

Conditions

Temperature: 45 °C

Procedure

Compound 59 (0.12 g, 0.196 mmol) was dissolved in MeOH (6 mL) and 2 M aqueous NaOH (3 mL) was added. The reaction mixture was stirred at 45° C. for 2.5 h and cooled down to 0° C. The mixture was neutralized with 5 N HCl to pH 3. After evaporation of solvent, the residue was dried under high vacuum and dissolved in DMF. After filtration, filtrate was concentrated by evaporation to a small volume and the product was separated by C18 reverse phase HPLC using buffer A (1% TFA in water) and buffer B (1% TFA acetonitrile) from 10% buffer B to 70% buffer B to provide a white solid (83%). MS (ESI) 599.18, 597.18 (M+H+).

Workup

temperaturecooled down to 0° C
customAfter evaporation of solvent
customthe residue was dried under high vacuum
dissolutiondissolved in DMF
filtrationAfter filtration, filtrate
concentrationwas concentrated by evaporation to a small volume
customthe product was separated by C18 reverse phase

Sources & evidence

ORD record: ord-77778860e16f401d9b40658ba80c116d
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304085B2

Reaction notes

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