3-Pyridinecarboxaldehyde → HCID 44548645, compound

HRID 707129Notes

Reaction equation

HRID 707129 reaction equation
OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[CH:15]12[O:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][N:17]([C:23]1[N:28]=[C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:26]=[C:25]([C:35]3[CH:40]=[CH:39][C:38]([NH:41][C:42]([NH:44][C:45]4[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=4)=[O:43])=[CH:37][CH:36]=3)[N:24]=1)[CH2:16]2.[N:51]1[CH:56]=[CH:55][CH:54]=[C:53]([CH:57]=O)[CH:52]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(N(CC)CC)C>[CH:19]12[O:22][CH:15]([CH2:21][CH2:20]1)[CH2:16][N:17]([C:23]1[N:28]=[C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH2:57][C:53]4[CH:52]=[N:51][CH:56]=[CH:55][CH:54]=4)[CH2:31][CH2:30]3)[N:26]=[C:25]([C:35]3[CH:36]=[CH:37][C:38]([NH:41][C:42]([NH:44][C:45]4[CH:46]=[CH:47][N:48]=[CH:49][CH:50]=4)=[O:43])=[CH:39][CH:40]=3)[N:24]=1)[CH2:18]2

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 130403997HCID 130403997, compound

Product 1

HCID 44548645HCID 44548645, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(piperazin-1-yl)-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea-2TFA (150 mg) in dichloromethane (4 mL) and triethylamine (0.12 mL) was treated with 3-pyridinecarboxaldehyde (0.1 mL), followed by sodium triacetoxyborohydride (80 mg). The mixture was concentrated to dryness and purified on HPLC to give the title compound as its tri-TFA salt; MS (ES+) 579.3 (M+H)+

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompurified on HPLC

Sources & evidence

ORD record
ord-c19a7c55624c4f559787b6543d8b6da3
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

Loading…