Hydrochloric Acid → 4-(Benzyloxy)-1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)pyridin-2(1H)-one hydrochloride

HRID 882017Notes

Reaction equation

HRID 882017 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[N:20]=[C:19]3[N:21]([CH3:28])[C:22]4[CH2:27][CH2:26][NH:25][CH2:24][C:23]=4[C:18]3=[CH:17][CH:16]=2)[C:11](=[O:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:30]>CO>[ClH:30].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[N:20]=[C:19]3[N:21]([CH3:28])[C:22]4[CH2:27][CH2:26][NH:25][CH2:24][C:23]=4[C:18]3=[CH:17][CH:16]=2)[C:11](=[O:29])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 575245054-(Benzyloxy)-1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)pyridin-2(1H)-one

Product 1

HCID 679705194-(Benzyloxy)-1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)pyridin-2(1H)-one hydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 4-(benzyloxy)-1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridin-2-yl)pyridin-2(1H)-one (0.24 g, 0.62 mmol) in MeOH (2.0 mL) was treated with 1.25 M HCl in MeOH (0.67 mL, 0.84 mmol), and the resulting solution was stirred at ambient temperature for 3 h. The solution was concentrated to dryness, diluted with H2O and lyophilized to yield the title compound (0.16 g, 60%) as an off-white powder: 1H NMR (500 MHz, DMSO-d6) δ 8.53 (br s, 1H), 8.02 (d, J=8.0 Hz, 1H), 7.81 (d, J=7.5 Hz, 1H), 7.49-7.41 (m, 4H), 7.40-7.32 (m, 2H), 6.17 (dd, J=7.5, 2.5 Hz, 1H), 5.99 (d, J=2.5 Hz, 1H), 5.17 (s, 2H), 4.27 (s, 2H), 3.70 (s, 3H), 3.46 (t, J=5.5 Hz, 2H), 3.05 (t, J=5.5 Hz, 2H); ESI MS m/z 387 [M+H]+; HPLC (Method A)>99% (AUC), tR=13.5 min.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. additiondiluted with H2O

Sources & evidence

ORD record
ord-87d404b387504ed08e36772746ef5b75
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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