HCID 67345256, compound → HCID 67344074, compound

HRID 1257673Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][N:18]=[C:17]3[N:24]([S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:25]=[CH:26][C:16]=23)[C@H:10]([F:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[C:20]([NH2:21])=[CH:19][N:18]=[C:17]3[N:24]([S:27]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)(=[O:29])=[O:28])[CH:25]=[CH:26][C:16]=23)[C@H:10]([F:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A stirred solution of trans-4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester (0.231 g, 0.445 mmol) in ethyl acetate (5 ml) was treated with 10% palladium on activated carbon (0.025 g, 0.023 mmol) and stirred at 50° C. overnight. The mixture was then filtered through Celite, washed with copious methanol and concentrated under vacuum to give 201 mg (92%) of trans-4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester that was used without further purification. LCMS (Method F): RT=0.88 min, m+H=490.0; 1H NMR (400 MHz, DMSO) δ=8.06-7.99 (m, 2H), 7.72-7.64 (m, 1H), 7.60 (s, 3H), 7.54-7.46 (m, 1H), 6.87-6.79 (m, 1H), 5.33-5.22 (m, 1H), 4.60-4.33 (m, 3H), 4.13-4.07 (m, 1H), 3.80-3.66 (m, 1H), 3.26-3.03 (m, 2H), 1.96-1.87 (m, 1H), 1.41 (s, 9H), 1.37-1.32 (m, 1H).

Workup

filtrationThe mixture was then filtered through Celite
washwashed with copious methanol
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a8e1993fbcb84a278beba3fa9728e7d6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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