Formaldehyde → HCID 86708776, compound

HRID 1751569Notes

Reaction equation

HRID 1751569 reaction equation
[CH3:1][CH:2]([CH3:59])[C@H:3]([NH:54][C:55](=[O:58])[O:56][CH3:57])[C:4](=[O:53])[N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[NH:35][C:34]([C@@H:36]6[CH2:40][CH2:39][CH2:38][N:37]6[C:41]([C@H:43]6[C:52]7[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=7)[CH2:46][CH2:45][NH:44]6)=[O:42])=[N:33][CH:32]=5)=[CH:27][CH:26]=4)[CH:21]=3)[CH:16]=2)=[CH:13][N:14]=1.[CH2:60]=O>[Zn].C(O)(=O)C>[CH3:1][CH:2]([CH3:59])[C@H:3]([NH:54][C:55](=[O:58])[O:56][CH3:57])[C:4]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[NH:35][C:34]([C@@H:36]6[CH2:40][CH2:39][CH2:38][N:37]6[C:41]([C@H:43]6[C:52]7[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=7)[CH2:46][CH2:45][N:44]6[CH3:60])=[O:42])=[N:33][CH:32]=5)=[CH:27][CH:26]=4)[CH:21]=3)[CH:16]=2)=[CH:13][N:14]=1)=[O:53]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 67682387HCID 67682387, compound

Product 1

HCID 86708776HCID 86708776, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(6-(4-(2-((S)-1-((R)-1,2,3,4-tetrahydroisoquinoline-1-carbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (135 mg, 0.17 mmol), acetic acid (1.7 mL), zinc dust (111 mg, 1.7 mmol), and formaldehyde were all mixed in round bottom flask and stirred at room temperature overnight. The crude mixture was filtered through a celite plug and the filtrate was concentrated down to dryness on rotovap. The residue was then taken up in EtOAc and washed with 10% Na2CO3 and brine and dried over MgSO4. The filtrate was then concentrated down and the residue was purified on reverse phase HPLC. (13 mg, 10%). MS (ESI) m/z 805.77 [M+H]+.

Workup

  1. additionall mixed in round bottom flask
  2. filtrationThe crude mixture was filtered through a celite plug
  3. concentrationthe filtrate was concentrated down to dryness on rotovap
  4. washwashed with 10% Na2CO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationThe filtrate was then concentrated down
  7. customthe residue was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-3b20482203004a329e53df5343f06c93
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…