1,1'-Carbonyl-di-(1,2,4-triazole) → HCID 118036489, compound

HRID 1778030Notes

Reaction equation

HRID 1778030 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([NH:10][C:11]23[CH2:15][CH:13]([CH2:14]2)[CH2:12]3)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.N1([C:21](N2C=NC=N2)=[O:22])C=NC=N1.[CH3:28][O:29][CH:30]([O:50][CH3:51])[C:31]1[C:40]([CH2:41][N:42]2[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][C:43]2=[O:49])=[CH:39][C:38]2[CH2:37][CH2:36][CH2:35][NH:34][C:33]=2[N:32]=1>CN(C=O)C>[C:11]12([NH:10][C:8]3[C:5]([C:6]#[N:7])=[CH:4][N:3]=[C:2]([NH:1][C:21]([N:34]4[C:33]5[C:38](=[CH:39][C:40]([CH2:41][N:42]6[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][C:43]6=[O:49])=[C:31]([CH:30]([O:50][CH3:51])[O:29][CH3:28])[N:32]=5)[CH2:37][CH2:36][CH2:35]4)=[O:22])[CH:9]=3)[CH2:14][CH:13]([CH2:15]1)[CH2:12]2

Participants

5

Reactant 3

HCID 43939611,1'-Carbonyl-di-(1,2,4-triazole)HCID 1180362016-Amino-4-(bicyclo[1.1.1]pentan-1-ylamino)nicotinonitrile2×HCID 1180366581-((2-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-4-methylpiperazin-2-one2×

Product 1

HCID 118036489HCID 118036489, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 6-amino-4-(bicyclo[1.1.1]pentan-1-ylamino)nicotinonitrile (intermediate 277, 61 mg, 0.305 mmol) in anhydrous DMF (1.5 ml) was added to a solution of di(1H-1,2,4-triazol-1-yl)methanone (50 mg, 0.305 mmol) in DMF (1.5 ml) at 0° C. After stirring for 1.5 h at room temperature a solution of 1-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-4-methylpiperazin-2-one (intermediate 81, 60 mg, 0.179 mmol) in DMF (1.5 ml) was added. The reaction mixture was stirred for 18 h at room temperature, then evaporated directly onto isolate and purified by normal phase chromatography: 12 g RediSep® silica column; eluting with EtOAc then a gradient from DCM to 10% MeOH in DCM. Product containing fractions were combined and evaporated to give the title compound as a yellow solid. (UPLC-MS 6) tR 1.00; ESI-MS 561.3 [M+H]+.

Workup

  1. additionwas added
  2. customevaporated directly
  3. customonto isolate
  4. custompurified by normal phase chromatography
  5. washeluting with EtOAc
  6. additionProduct containing fractions
  7. customevaporated

Sources & evidence

ORD record
ord-5e52f2b7bfc848b29eabd3fb695c41f6
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…