Triethylamine → HCID 69675558, compound

HRID 1751548Notes

Reaction equation

HRID 1751548 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:30]=[C:29]3[C:21]([C:22]4[CH:23]=[CH:24][C:25]([C:33]5[CH:34]=[CH:35][C:36]6[N:40]=[C:39]([C@@H:41]7[CH2:49][C:44]8([O:48][CH2:47][CH2:46][O:45]8)[CH2:43][N:42]7C(OCC7C=CC=CC=7)=O)[NH:38][C:37]=6[CH:60]=5)=[CH:26][C:27]=4[C:28]3([F:32])[F:31])=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>C(OCC)(=O)C.[Pd]>[O:48]1[C:44]2([CH2:49][C@@H:41]([C:39]3[NH:38][C:37]4[CH:60]=[C:33]([C:25]5[CH:26]=[C:27]6[C:22]([C:21]7[CH:20]=[CH:19][C:18]([C:15]8[NH:14][C:13]([C@@H:9]9[CH2:10][CH2:11][CH2:12][N:8]9[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:17][CH:16]=8)=[CH:30][C:29]=7[C:28]6([F:31])[F:32])=[CH:23][CH:24]=5)[CH:34]=[CH:35][C:36]=4[N:40]=3)[NH:42][CH2:43]2)[O:45][CH2:46][CH2:47]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86708766HCID 86708766, compound

Product 1

HCID 69675558HCID 69675558, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-Benzyl 8-(6-(7-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate (375 mg, 0.46 mmol) was dissolved in ethyl acetate (10 mL) and to it was added triethyl amine (140 mg, 1.38 mmol), followed by 10% Pd/C (Pearlman's catalyst) (196 mg, 0.09 mmol). The flask was purged with hydrogen gas three times by applying vacuum and purging hydrogen gas from a balloon and the mixture was stirred overnight at room temperature. The crude product was filtered through a 0.2 micron Nylon filter member and the filtrate was concentrated down on rotovap. (229 mg, 73%).

Workup

  1. customThe flask was purged with hydrogen gas three times
  2. custompurging hydrogen gas from a balloon
  3. filtrationThe crude product was filtered through a 0.2 micron Nylon
  4. filtrationfilter member
  5. concentrationthe filtrate was concentrated down on rotovap

Sources & evidence

ORD record
ord-3a9b5e517ebe4200a0f8c8d0f0980133
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…