Hydrochloric Acid → HCID 68694688, compound

HRID 2234700Notes

Reaction equation

C[O:2][C:3](=[O:46])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[C:23]5[C:27]=4[NH:26][CH:25]=[CH:24]5)=[CH:17][N:16](S(C4C=CC(C)=CC=4)(=O)=O)[C:13]3=[N:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].[OH-].[K+].Cl>CO>[C:42]([O:41][C:39]([NH:38][C:5]1[CH:6]=[CH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[C:23]5[C:27]=4[NH:26][CH:25]=[CH:24]5)=[CH:17][NH:16][C:13]3=[N:14][CH:15]=2)=[CH:9][C:4]=1[C:3]([OH:46])=[O:2])=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

Conditions

Temperature: 40 °C

Procedure

2-tert-Butoxycarbonylamino-5-[3-(1H-indol-7-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid methyl ester (605 mg, 0.95 mmol) was suspended in methanol (10 mL), potassium hydroxide (50% w/v in water, 2 mL) was added and the resulting suspension was heated to 40° C. for 1 hour. Hydrochloric acid (1 N) was added to adjust the pH to 6. The mixture was extracted with ethyl acetate (10 mL×4). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was triturated with hexane to afford 2-tert-butoxycarbonylamino-5-[3-(1H-indol-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid as a pale yellow powder (308 mg, 69%). MS: m/z 469 (M+H+).

Workup

extractionThe mixture was extracted with ethyl acetate (10 mL×4)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was triturated with hexane

Sources & evidence

ORD record: ord-181dfb56967b458f9932f822d8a985cf
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709645B2

Reaction notes

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