Hydrochloric Acid → 4-(Benzyloxy)-1-(1,2,3,4-tetrahydropyrido[4',3':4,5]imidazo[1,2-a]pyridin-7-yl)pyridin-2(1H)-one hydrochloride

HRID 882068Notes

Reaction equation

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

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 67988851tert-Butyl 7-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate

Product 1

HCID 679705744-(Benzyloxy)-1-(1,2,3,4-tetrahydropyrido[4',3':4,5]imidazo[1,2-a]pyridin-7-yl)pyridin-2(1H)-one hydrochlorideYield 82%

Procedure

tert-Butyl 7-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3,4-dihydropyrido[4′,3′:4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate (482 mg, 1.02 mmol) was deprotected and converted to the hydrochloride according to Example 18 (step h) to provide the title compound (340 mg, 82%) as a white solid: mp 280° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.93 (s, 2H), 8.54 (d, J=7.2 Hz, 1H), 7.77 (s, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.47-7.34 (m, 5H), 7.23 (d, J=6.6 Hz, 1H), 6.19 (dd, J=7.6, 2.5 Hz, 1H), 6.02 (d, J=2.5 Hz, 1H), 5.16 (s, 2H), 4.57 (s, 2H), 3.51 (s, 2H), 3.08 (t, J=5.4 Hz, 2H); ESI MS m/z 373 [M+H]; HPLC (Method B) 98.8% (AUC), tR=10.6 min.

Sources & evidence

ORD record: ord-714577210f464391a65a8ebfef29aad3
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993765B2

Reaction notes

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