Hydrochloric Acid → 4-(Benzyloxy)-1-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[3,2-c]azepin-2-yl)pyridin-2(1H)-one hydrochloride

HRID 474990Notes

Reaction equation

HRID 474990 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[C:22]4[CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH2:26][CH2:27][C:21]=4[N:20]([CH3:35])[C:19]=3[N:36]=2)[C:11](=[O:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:38]>CO>[ClH:38].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[C:22]4[CH2:23][NH:24][CH2:25][CH2:26][CH2:27][C:21]=4[N:20]([CH3:35])[C:19]=3[N:36]=2)[C:11](=[O:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66869329tert-Butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-10-methyl-7,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[3,2-c]azepine-6(5H)-carboxylate

Product 1

HCID 668737564-(Benzyloxy)-1-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[3,2-c]azepin-2-yl)pyridin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of tert-butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-10-methyl-7,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[3,2-c]azepine-6(5H)-carboxylate (140 mg, 0.028 mmol) in 1.25 M HCl in MeOH (6.0 mL) was stirred under N2 at ambient temperature for 18 h. Additional 1.25 M HCl in MeOH was added, and the solution was stirred at ambient temperature for 18 h. The solution was concentrated to dryness to yield the title compound (130 mg, quant.) as a light-yellow powder: mp 328-332° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.20 (s, 2H), 8.16 (d, J=8.0 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.48-7.41 (m, 4H), 7.38-7.34 (m, 2H), 6.17 (dd, J=7.5, 2.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 5.17 (s, 2H), 4.46 (s, 2H), 3.75 (s, 3H), 3.44-3.43 (m, 2H), 3.14-3.12 (m, 2H), 2.09-2.07 (m, 2H); ESI MS m/z 401 [M+H]+; HPLC (Method A)>99% (AUC), tR=13.3 min.

Workup

  1. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-1242135680e4496889d271650e407595
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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