Butyl isocyanate → HCID 178449840, compound

HRID 2118244Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:29])[CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([N:19]3[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][OH:28])[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[N:6][CH:7]=1.[CH3:30][CH2:31][CH2:32][CH2:33][N:34]=[C:35]=[O:36]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:29])[CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([N:19]3[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][O:28][C:35](=[O:36])[NH:34][CH2:33][CH2:32][CH2:31][CH3:30])[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.10 g (0.21 mmol) of trans-(4-{2-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-ethyl}-cyclohexyl)-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone in 2 mL of CH2Cl2 was cooled (0° C.) and treated with 0.048 mL (0.43 mmol, 2 eq) of N-butyl isocyanate. After 20 h and 48 h the reaction was again cooled (0° C.) and treated with 0.048 mL (0.43 mmol, 2.0 eq) and 0.024 mL (0.21 mmol, 2.0 eq) of N-butyl isocyanate, respectively. The reaction was evaporated and dissolved in 5 mL of CH2Cl2/0.5 mL of MeOH and stirred for 1.5 h. After evaporation, the reaction was purified by flash-chromatography on 5 g silica gel (CH2Cl2:MeOH 99:1 to 4:1) to give 0.081 g (68%) of pure trans-butyl-carbamic acid 2-[4-(4-{2-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-ethyl}-cyclohexanecarbonyl)-[1,4]diazepan-1-yl]-ethyl ester, MS: 567 (MH+, 1Br).

Workup

customThe reaction was evaporated
dissolutiondissolved in 5 mL of CH2Cl2/0.5 mL of MeOH
customAfter evaporation
customthe reaction was purified by flash-chromatography on 5 g silica gel (CH2Cl2:MeOH 99:1 to 4:1)

Sources & evidence

ORD record: ord-2df91fe234b44fcf9d9c3ccbd1190e7c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442791B2

Reaction notes

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