Sodium Iodide → 4-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 1360193Notes

Reaction equation

[CH3:1][C:2]1([CH3:11])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][NH2:10].Cl[C:13]1[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]2[NH:22][CH:23]=[CH:24][C:14]=12.[I-].[Na+].CN(C)C=O>CN1CCCC1=O.C(N(CC)CC)C.O>[CH3:1][C:2]1([CH3:11])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][NH:10][C:13]1[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]2[NH:22][CH:23]=[CH:24][C:14]=12

Participants

Conditions

Temperature: 130 °C

Procedure

To 1-[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methaneamine (61 mg) were added a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (39 mg) in 1-methyl-2-pyrrolidone (0.6 ml), triethylamine (0.056 ml), and sodium iodide (3 mg), and the mixture was stirred at 130° C. for 17 hours. After the reaction mixture was left to cool, to the reaction mixture were added N,N-dimethylformamide (0.3 ml) and water (0.1 ml), and the reaction mixture was dissolved. The reaction mixture was directly purified by preparative HPLC (101M-NH4HCO3+NH3 (pH=9.2):CH3CN=98:2 to 30:70). The active fraction was concentrated and dried to hardness to obtain 4-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (33.5 mg) as a solid.

Workup

waitAfter the reaction mixture was left
temperatureto cool, to the reaction mixture
dissolutionthe reaction mixture was dissolved
customThe reaction mixture was directly purified by preparative HPLC (101M-NH4HCO3+NH3 (pH=9.2):CH3CN=98:2 to 30:70)
concentrationThe active fraction was concentrated
customdried to hardness

Sources & evidence

ORD record: ord-0ffe5c77e5a444b2875ab9dd2e75e92f
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879844B2

Reaction notes

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