Trifluoroacetic acid → HCID 178444052, compound

HRID 923589Notes

Reaction equation

HRID 923589 reaction equation
[CH2:1]([O:8][C:9]1[CH:54]=[CH:53][C:12]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([CH2:23][N:24]([CH2:45][C:46]([O:48]C(C)(C)C)=[O:47])[C:25](=[O:44])[C:26]4[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:43])[CH2:34][C:35]5[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=5)=[CH:28][CH:27]=4)=[CH:22][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:54]=[CH:53][C:12]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([CH2:23][N:24]([CH2:45][C:46]([OH:48])=[O:47])[C:25](=[O:44])[C:26]4[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:43])[CH2:34][C:35]5[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=5)=[CH:28][CH:27]=4)=[CH:22][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178444051HCID 178444051, compound

Product 1

HCID 178444052HCID 178444052, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 2-(N-((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate INT-49 (40 mg, 0.055 mmol) in DCM (2 mL) was added TFA (1 mL). After stirring at room temperature for 2 h, the solvents were concentrated and the residue purified by preparative HPLC to afford 15 mg (40%) of 2-(N-((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetic acid 366 as a white powder. LCMS-ESI (m/z) calculated for C40H44N4O6: 676; found 677 [M+H]+, tR=6.77 min (Method 4). 1H NMR (400 MHz, DMSO) 12.82 (br s, 1H), 12.21 (br s, 1H), 10.29 (s, 1H), 7.65 (d, J=8.2 Hz, 2H), 7.30-7.57 (m, 4H), 7.27-7.15 (m, 4H), 7.15-6.92 (m, 1H), 6.89-6.75 (m, 4H), 4.71 (s, 1H), 4.62 (s, 1H), 4.08 (s, 2H), 3.91 (m, 3H), 3.81-3.69 (m, 4H), 3.57 (s, 2H), 1.73-1.61 (m, 2H), 1.43-1.20 (m, 8H), 0.90-0.80 (m, 3H).

Workup

  1. concentrationthe solvents were concentrated
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-abce9113e1494551a340f6a201e328c4
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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