Hydrochloric Acid → HCID 68657265, compound

HRID 930661Notes

Reaction equation

HRID 930661 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]4[CH2:28][CH2:27][N:26]([C:29]([C@@H:31]5[CH2:35][CH2:34][CH2:33][N:32]5C(OC(C)(C)C)=O)=[O:30])[CH2:25][C:20]=4[N:21]3[CH3:24])=[CH:17][CH:16]=2)[C:11](=[O:43])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:44]>CO.CCOCC>[ClH:44].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]4[CH2:28][CH2:27][N:26]([C:29]([C@@H:31]5[CH2:35][CH2:34][CH2:33][NH:32]5)=[O:30])[CH2:25][C:20]=4[N:21]3[CH3:24])=[CH:17][CH:16]=2)[C:11](=[O:43])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57950443HCID 57950443, compound

Product 1

HCID 68657265HCID 68657265, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(S)-tert-Butyl 2-(7-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-2-carbonyl)pyrrolidine-1-carboxylate (55 mg, 0.094 mmol) was stirred in a mixture of MeOH (2 mL) and 2 N HCl in Et2O (8 mL) for 5 h. The reaction mixture was concentrated to provide the title compound (42 mg, 85%) as a yellow-green solid: mp 220-226° C.; 1H NMR (500 MHz, CD3OD) δ 7.79 (dd, J=7.5, 1.4 Hz, 1H), 7.47 (d, J=8.3 Hz, 1H), 7.49-7.46 (m, 3H), 7.44-7.46 (m, 2H), 7.39-7.36 (m, 1H), 7.04 (dd, J=8.3, 1.6 Hz, 1H), 6.57-6.55 (m, 1H), 6.34 (d, J=2.5 Hz, 1H), 5.27 (s, 2H), 4.96-4.87 (m, 2H), 3.90-8.86 (m, 2H), 3.77 (s, 3H), 3.48-3.34 (m, 3H), 3.00-2.86 (m, 2H), 2.67-2.61 (m, 1H), 2.17-2.02 (m, 3H); ESI MS m/z 483 [M+H]+; HPLC (Method B) 95.5% (AUC), tR=13.5 min.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-bab591ccba184cc68f58cff8ee85cd37
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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