Dichloromethane → HCID 67045612, compound

HRID 1034824Notes

Reaction equation

C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[N:21](C(OC(C)(C)C)=O)[CH:22]=[C:23]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[C:16]=23)[CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:45]>>[ClH:45].[NH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][CH:22]=[C:23]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[C:16]=23)[CH2:10]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 67045132HCID 67045132, compound

Product 1

HCID 67045612HCID 67045612, compoundYield 27%

Procedure

(R)-tert-Butyl 4-(3-(tert-butoxycarbonylamino)piperidin-1-yl)-3-isobutyramido-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (0.010 g, 0.020 mmol; Example 81, Step B) was placed in DCM (3 mL) at room temperature. TFA (1 mL) was then added, and the reaction was stirred at room temperature for 1 hour and concentrated to dryness. The resulting residue was then purified by reverse phase chromatography (Biotage SP4, C-18 12M+, 0-50% ACN in water). The resulting product was next dissolved in minimal DCM (with MeOH to aid solubility) and added to a stirred solution of 1M HCl in ether. The resulting solid was filtered, washed with ether and dried to give (R)—N-(4-(3-aminopiperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isobutyramide hydrochloride (0.002 g, 27% yield). LCMS (APCI+) m/z 302 (M+H)+.

Workup

concentrationconcentrated to dryness
customThe resulting residue was then purified by reverse phase chromatography (Biotage SP4
dissolutionThe resulting product was next dissolved in minimal DCM (with MeOH to aid solubility)
additionadded to a stirred solution of 1M HCl in ether
filtrationThe resulting solid was filtered
washwashed with ether
customdried

Sources & evidence

ORD record: ord-b82a9500b7ce428aa8a91505649e80f0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08545897B2

Reaction notes

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