Dichloromethane → HCID 67045526, compound

HRID 2203911Notes

Reaction equation

C(O)(C(F)(F)F)=O.[Br:8][C:9]1[C:10]([N:36]2[CH2:41][CH2:40][CH2:39][C@@H:38]([N:42](C(OC(C)(C)C)=O)[CH3:43])[CH2:37]2)=[C:11]2[C:17]([NH:18][C:19]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=3)=[O:20])=[CH:16][N:15](C(OC(C)(C)C)=O)[C:12]2=[N:13][CH:14]=1.C(Cl)[Cl:52]>>[ClH:52].[Br:8][C:9]1[C:10]([N:36]2[CH2:41][CH2:40][CH2:39][C@@H:38]([NH:42][CH3:43])[CH2:37]2)=[C:11]2[C:17]([NH:18][C:19]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=3)=[O:20])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 67045967HCID 67045967, compound

Product 1

HCID 67045526HCID 67045526, compoundYield 91%

Procedure

TFA (0.020 mL, 0.26 mmol) was added to (R)-tert-butyl 5-bromo-4-(3-(tert-butoxycarbonyl(methyl)amino)piperidin-1-yl)-3-(1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamido)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (0.034 g, 0.052 mmol) in DCM (1 mL). The reaction mixture was stirred at room temperature for 1 hour. The solvent was removed. The residue was dissolved in DCM (1 mL), and 2N HCl in ether (3 mL) was added. The solid formed was collected to give (R)—N-(5-bromo-4-(3-(methylamino)piperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide hydrochloride (25 mg, 91%) as a solid. 1H NMR (400 MHz, D2O) δ 8.34 (s, 1H), 8.30 (s, 1H), 7.97 (dd, 1H), 7.35 (s, 1H), 6.60 (d, 1H), 3.88 (m, 1H), 3.53 (s, 3H), 3.39 (m, 2H), 3.08 (m, 2H), 2.55 (s, 3H), 2.04 (m, 1H), 1.68 (m, 1H), 1.60 (m, 1H), 1.35 (m, 1H). LCMS (APCI+) m/z 459 (M+H)+.

Workup

customThe solvent was removed
dissolutionThe residue was dissolved in DCM (1 mL)
addition2N HCl in ether (3 mL) was added
customThe solid formed
customwas collected

Sources & evidence

ORD record: ord-a8964d5e9ed141a6863c43d36ee11395
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365568B2

Reaction notes

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