Dichloromethane → HCID 178474990, compound

HRID 1963962Notes

Reaction equation

HRID 1963962 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 lyophilization 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, 6 H) 1.70 (d, J=12.89 Hz, 2 H) 1.92 (s, 3 H) 1.93-2.06 (m, 3 H) 2.10 (br. s., 2 H) 3.28-3.32 (dMeOH, 2H App.) 3.34-3.47 (m, 2 H) 3.55-3.73 (m, 2 H) 3.94 (dd, J=11.28, 3.08 Hz, 2 H) 7.00 (s, 1 H) 7.94 (s, 2 H) 8.01 (s, 1 H).

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-99eb1a0d71cf4bc29e296248a334cf57
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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