Hydrochloric Acid → HCID 68656831, compound

HRID 930791Notes

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:19]4[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24][C:20]=4[NH:21][C:22]=3[CH:23]=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].[ClH:36].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[C:19]4[CH2:27][NH:26][CH2:25][CH2:24][C:20]=4[NH:21][C:22]=3[CH:23]=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 57950402HCID 57950402, compound

Product 1

HCID 68656831HCID 68656831, compoundYield 26%

Procedure

Prepared from tert-butyl 7-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (150 mg, 0.32 mmol) according to the procedure of Example 1 (step d). Purification by flash column chromatography (4 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 85% methylene chloride over 30 min) provided the free-base as a yellow solid. This was converted to the bis-HCl salt (2 N HCl/Et2O in CH2Cl2) providing the title compound (36 mg, 26%) as a yellow solid: mp 240° C. dec.; 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=7.5 Hz, 1H), 7.57 (d, J=8.2 Hz, 1H), 7.47 (d, J=7.2 Hz, 2H), 7.42-7.36 (m, 4H), 7.03 (d, J=8.5 Hz, 1H), 6.39 (dd, J=7.6, 2.5 Hz, 1H), 6.21 (d, J=2.5 Hz, 1H), 5.21 (s, 2H), 4.47 (s, 2H), 3.64 (t, J=6.0 Hz, 2H), 3.20 (t, J=6.1 Hz, 2H); ESI MS m/z 372 [M+H]+; HPLC (Method A) 95.0% (AUC), tR=12.2 min.

Workup

customPurification by flash column chromatography (4 g ISCO column
washeluting with methylene chloride
customgradient 100% methylene chloride to 85% methylene chloride over 30 min) provided the free-base as a yellow solid

Sources & evidence

ORD record: ord-93aa841742864ede805cc711cab5f39d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296743B2

Reaction notes

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