2,4-Dichloro-1,3,5-triazine → HCID 68442457, compound

HRID 1929780Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][C@@H:9]([NH2:12])[CH2:8]1)=[O:6])[CH:2]=[CH2:3].Cl[C:14]1[N:19]=[C:18](Cl)[N:17]=[CH:16][N:15]=1.[C:21]([O:25][C:26](=[O:35])[NH:27][CH:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][C@@H:9]([NH:12][C:14]2[N:19]=[C:18]([NH:34][CH:31]3[CH2:32][CH2:33][CH:28]([NH:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:35])[CH2:29][CH2:30]3)[N:17]=[CH:16][N:15]=2)[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

(R)-3-Amino-pyrrolidine-1-carboxylic acid allyl ester (1 eq.) is dissolved in DCM. The reaction mixture is cooled to 0° C. and a solution of 2,4-dichloro-[1,3,5]triazine (1 eq.) in DCM is added dropwise. The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is re-cooled to 0° C. and a solution of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1 eq.) in DCM is added dropwise. The reaction mixture is stirred at room temperature overnight. The reaction mixture is partitioned between (0.2 M) HCl(aq) and DCM. The organics are washed with water, saturated NaHCO3(aq) and brine. The combined organics are dried (MgSO4), filtered and reduced in vacuo, to yield the title compound.

Workup

temperatureThe reaction mixture is re-cooled to 0° C.
stirringThe reaction mixture is stirred at room temperature overnight
customThe reaction mixture is partitioned between (0.2 M) HCl(aq) and DCM
washThe organics are washed with water, saturated NaHCO3(aq) and brine
dry with materialThe combined organics are dried (MgSO4)
filtrationfiltered

Sources & evidence

ORD record: ord-50883605084c42f4b531ea2a6f41316c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188100B2

Reaction notes

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