Hydrochloric Acid → HCID 66873989, compound

HRID 474927Notes

Reaction equation

HRID 474927 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]1[C:18]1[CH:19]=[CH:20][C:21]2[C:22]3[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28][CH2:27][C:23]=3[NH:24][C:25]=2[CH:26]=1.[ClH:39]>CO>[ClH:39].[CH2:31]1[C:22]2[C:21]3[CH:20]=[CH:19][C:18]([N:3]4[CH:4]=[CH:5][C:6]([C:8]5[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=5)=[CH:7][C:2]4=[O:1])=[CH:26][C:25]=3[NH:24][C:23]=2[CH2:27][CH2:28][CH2:29][NH:30]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70805202HCID 70805202, compound

Product 1

HCID 66873989HCID 66873989, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 8-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (30 mg, 0.057 mmol) was treated with 1.25 M HCl in MeOH (5.5 mL), and the resulting solution was stirred at ambient temperature for 18 h. The solution was partially concentrated and diluted with Et2O. The resulting solids were collected by filtration, washed with Et2O and dried to yield the title compound (13 mg, 51%) as a yellow powder: mp 310-320° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 11.51 (s, 1H), 9.14 (s, 1H), 8.81 (s, 2H), 8.39 (dd, J=8.5, 2.0 Hz, 1H), 8.34 (d, J=8.5 Hz, 1H), 7.82 (d, J=7.5 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.41 (d, J=2.0 Hz, 1H), 7.26 (d, J=2.0 Hz, 1H), 7.08-7.04 (m, 2H), 4.44 (s, 2H), 3.49-3.47 (m, 2H), 3.06-3.04 (m, 2H), 2.03-2.01 (m, 2H); ESI MS m/z 425 [M+H]+; HPLC (Method A) 96.9% (AUC), tR=13.7 min.

Workup

  1. concentrationThe solution was partially concentrated
  2. additiondiluted with Et2O
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-bc63e40c9b4b4817a822b9854d830636
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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