Hydrochloric Acid → HCID 86280703, compound

HRID 1776746Notes

Reaction equation

HRID 1776746 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][C:26]([O:28][CH2:29][C:30]5[CH:39]=[CH:38][C:37]6[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=6)[N:31]=5)=[CH:27][C:22]=4[N:21]=[C:20]3[CH2:40][C:41]3([C:46]([O:48]CC)=[O:47])[CH2:45][CH2:44][CH2:43][CH2:42]3)[CH:13]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C1COCC1.[Li+].[OH-].Cl>C(Cl)Cl.O.CO>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][C:26]([O:28][CH2:29][C:30]5[CH:39]=[CH:38][C:37]6[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=6)[N:31]=5)=[CH:27][C:22]=4[N:21]=[C:20]3[CH2:40][C:41]3([C:46]([OH:48])=[O:47])[CH2:45][CH2:44][CH2:43][CH2:42]3)[CH:13]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90414424HCID 90414424, compound

Product 1

HCID 86280703HCID 86280703, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 20 mL vial were added ethyl 1-((1-((4′-(methylsulfonamido)-[1,1′-biphenyl]-3-yl)methyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate (117 mg, 0.17 mmol), THF (2 mL) and MeOH (2 mL) followed by LiOH (1 mL, 1 M). The reaction vial was capped and the mixture was stirred at RT for 16 h. The mixture was cooled to RT, water (5 mL) was added and the pH was adjusted to ˜4 using 1 M HCl. To the mixture was added DCM (5 mL) and the mixture was stirred for 1 h at RT. The organic layer was separated then concentrated to dryness. The resulting residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C38H36N4O6S, 660.24; m/z found, 661.3 [M+H]+. (500 MHz; DMSO-d6) δ 8.39 (d, J=8.5, 1H), 8.03 (d, J=8.2, 1H), 7.98 (d, J=8.2, 1H), 7.81-7.76 (m, 1H), 7.69 (d, J=8.5, 1H), 7.63-7.59 (m, 1H), 7.56-7.50 (m, 3H), 7.40-7.34 (m, 3H), 7.29-7.25 (m, 2H), 7.20-7.18 (m, 1H), 7.02-6.99 (m, 1H), 6.95-6.91 (m, 1H), 5.50 (s, 2H), 5.37 (s, 2H), 3.16 (s, 2H), 3.01 (s, 3H), 2.16-2.09 (m, 2H), 1.72-1.52 (m, 6H).

Workup

  1. customThe reaction vial was capped
  2. temperatureThe mixture was cooled to RT
  3. stirringthe mixture was stirred for 1 h at RT
  4. customThe organic layer was separated
  5. concentrationthen concentrated to dryness
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-62764eb57eb946cd916880f0688a632a
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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