Dichloromethane → HCID 178474990, compound

HRID 1623418Notes

Reaction equation

HRID 1623418 reaction equation
[Cl:1][C:2]1[C:3]([C:16]2[CH:21]=[N:20][CH:19]=[C:18]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:17]=2)=[CH:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.C(Cl)Cl.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C1COCC1>[Cl:1][C:2]1[C:3]([C:16]2[CH:21]=[N:20][CH:19]=[C:18]([NH:22][CH2:23][CH:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[N:17]=2)=[CH:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:33](=[O:35])[CH3:34])[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 178511597HCID 178511597, compound

Product 1

HCID 178474990HCID 178474990, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of trans-N1-(5-chloro-4-(6-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazin-2-yl)pyridin-2-yl)cyclohexane-1,4-diamine (example 85) (14 mg, 0.034 mmol), DCM (0.5 ml), THF (0.500 ml), TEA (0.014 ml, 0.101 mmol) and acetic anhydride (3.48 μl, 0.037 mmol) was stirred at ambient temperature for 1 hour, and the reaction progress was followed by LCMS. The solvent was concentrated off, added 1.0 ml of DMSO, filtered and purified by prep LC. After lypohilization 6.3 mg of title compound was obtained as a TFA salt. LCMS (m/z): 445.2 (MH+), retention time=0.59 min.; 1H NMR (300 MHz, METHANOL-d4, 25° C.) δ ppm 1.21-1.55 (m, 6H) 1.70 (d, J=12.89 Hz, 2H) 1.92 (s, 3H) 1.93-2.06 (m, 3H) 2.10 (br. s., 2H) 3.28-3.32 (dMeOH, 2H App.) 3.34-3.47 (m, 2H) 3.55-3.73 (m, 2H) 3.94 (dd, J=11.28, 3.08 Hz, 2H) 7.00 (s, 1H) 7.94 (s, 2H) 8.01 (s, 1H).

Workup

  1. concentrationThe solvent was concentrated off
  2. additionadded 1.0 ml of DMSO
  3. filtrationfiltered
  4. custompurified by prep LC

Sources & evidence

ORD record
ord-b82335b922cd4391bd7cad7cabe32e58
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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