Dichloromethane → HCID 67045612, compound

HRID 2203906Notes

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-55fc71e0a844451c809a5935c9ba0ffb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365568B2

Reaction notes

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