Acetone → HCID 67045028, compound

HRID 1923702Notes

Reaction equation

[CH3:1][C:2](=O)[CH3:3].[ClH:5].[NH2:6][CH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[C:18](Br)=[CH:17][N:16]=[C:15]3[NH:20][CH:21]=[C:22]([NH:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=4)[C:14]=23)[CH2:9]1>>[ClH:5].[Cl:5][C:18]1[C:13]([N:10]2[CH2:11][CH2:12][CH2:8][C@@H:7]([NH:6][CH:2]([CH3:3])[CH3:1])[CH2:9]2)=[C:14]2[C:22]([NH:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=3)=[CH:21][NH:20][C:15]2=[N:16][CH:17]=1

Participants

Reactant 2

HCID 180Acetone

HCID 67045227HCID 67045227, compound

Product 1

HCID 67045028HCID 67045028, compoundYield 64%

Procedure

(R)-N-(5-Chloro-4-(3-(isopropylamino)piperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide hydrochloride (30 mg, 64% yield) was prepared as described in Example 6, using propan-2-one (104 mg, 1.80 mmol) and substituting (R)-N-(4-(3-aminopiperidin-1-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide hydrochloride (43 mg, 0.089 mmol) for (S)-N-(4-(3-(aminomethyl)pyrrolidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide hydrochloride. 1H NMR (400 MHz, D2O) δ 9.20-9.19 (m, 1H), 8.88-8.83 (m, 2H), 8.17 (s, 1H), 8.05-7.80 (m, 1H), 7.44-7.43 (m, 1H), 3.86-3.73 (m, 1H), 3.50-3.44 (m, 1H), 3.41-3.31 (m, 2H), 3.18-3.10 (m, 1H), 3.06-2.98 (m, 1H), 2.04-1.95 (m, 1H), 1.69-1.61 (m, 1H), 1.58-1.47 (m, 1H), 1.35-1.25 (m, 1H), 1.14 (d, 3H), 1.10 (d, 3H); LCMS (APCI+) m/z 413.1 (M+H)+, Retention time=2.06 minutes (Method 2).

Sources & evidence

ORD record: ord-695b44b2d07843a6ac9d9ba673099c62
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178131B2

Reaction notes

Loading…