Thionyl Chloride → HCID 68732742, compound

HRID 628679Notes

Reaction equation

HRID 628679 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([CH2:12][N:13]([CH:26]3[C:35]4[N:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH2:29][CH2:28][CH2:27]3)[CH2:14][CH2:15][CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:38])=O>CO>[ClH:38].[ClH:38].[ClH:38].[ClH:38].[NH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:13]([CH2:12][C:10]1[N:9]=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=1)[CH:26]1[C:35]2[N:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59176603HCID 59176603, compound2×

Product 1

HCID 68732742HCID 68732742, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)-amino)butylcarbamate, 10 (0.85 g, 1.80 mmol) in methanol (20 mL) was added thionyl chloride (1.27 g, 10.7 mmol) at room temperature. The reaction mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo yielding 790 mg (85%) of Z: 1H NMR (400 MHz, d6-DMSO) δ 10.78, (bs, 1H), 8.93, (s, 1H), 8.51 (d, J=4.4 Hz, 1H), 8.25-8.06 (m, 3H), 7.84, (d, J=7.6 Hz, 2H), 7.71, (d, J=7.2 Hz, 2H), 7.62-7.55 (m, 2H), 7.52-7.46, (m, 1H), 7.40-7.35, (m, 1H), 4.77, (m, 1H), 4.50-4.38, (m, 2H), 3.32-3.22, (m, 1H), 3.15-3.02 (m, 1H), 2.88-2.66 (m, 4H), 2.50-2.39 (m, 1H), 2.15-2.00, (m, 2H), 1.95-1.68, (m, 3H), 1.64-1.50, (m, 2H), ESI+ MS: m/z (rel intensity) 377 (100, M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customyielding 790 mg (85%) of Z

Sources & evidence

ORD record
ord-4785d2f586cb403c8e1f217e5de962af
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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