Tetrahydrofuran → HCID 67324832, compound

HRID 1257742Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]3[N:23]([S:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:28])=[O:27])[CH:24]=[CH:25][C:15]=23)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1>[Pd].CCO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[C:19]([NH2:20])=[CH:18][N:17]=[C:16]3[N:23]([S:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:28])=[O:27])[CH:24]=[CH:25][C:15]=23)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of (R)-3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (9.90 g, 20.3 mmol) and palladium on carbon (1.0 g, 10%, wet, Degussa, E101 NE/W) in a 4:1 mixture of THF and EtOH (150 ml) was stirred under a hydrogen atmosphere (2 balloons) at 50° C. for 18 h. The reaction mixture was cooled to 25° C. and was filtered through Celite. The Celite was washed with THF (1×20 ml), and the combined filtrate and washings were concentrated under reduced pressure to give (R)-3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (9.81 g, 99%) as a brown foam. LCMS (Method G, ESI): RT=0.83 min, m+H=458.3. This material was used in the next step below without additional purification or characterization.

Workup

temperatureThe reaction mixture was cooled to 25° C.
filtrationwas filtered through Celite
washThe Celite was washed with THF (1×20 ml)
concentrationthe combined filtrate and washings were concentrated under reduced pressure

Sources & evidence

ORD record: ord-d6160b32aaf445329cd37e15e082e7cb
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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