Isopropyl Isothiocyanate → HCID 86703984, compound

HRID 1773905Notes

Reaction equation

HRID 1773905 reaction equation
[CH3:1][C:2]1[N:11]2[C:5]([CH:6]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10]2)=[N:4][C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.[CH:40]([N:43]=[C:44]=[S:45])([CH3:42])[CH3:41]>C(#N)C>[CH:40]([NH:43][C:44]([NH:30][C:27]1[CH:28]=[CH:29][C:24]([C:3]2[N:4]=[C:5]3[N:11]([CH2:10][CH2:9][C:8]4[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=4[CH:6]3[O:16][CH:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)[C:2]=2[CH3:1])=[CH:25][CH:26]=1)=[S:45])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 75263Isopropyl IsothiocyanateHCID 81531DiisopropylethylamineHCID 86703979HCID 86703979, compound

Product 1

HCID 86703984HCID 86703984, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[1-methyl-4-(1-methyl piperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenylamine (example 173) (50 mg, 0.124 mmole) in ACN (1 mL) are added DIEA (65 μL, 0.372 mmole) and isopropylisothiocyanate (18.8 mg, 0.182 mmole). The reaction mixture is heated overnight at 80° C. Solvent is removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH:NH4OH) from (98:2:02) to (96.5:3.5:0.35) to give 1-isopropyl-3-{4-[1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diazabenzo[f]azulen-2-yl]-phenyl}-thiourea. [M+H]+=504.37.

Workup

  1. customSolvent is removed under reduced pressure
  2. customThe residue is purified by silica gel chromatography
  3. washeluting with (CH2Cl2:MeOH:NH4OH) from (98:2:02) to (96.5:3.5:0.35)

Sources & evidence

ORD record
ord-59d65d7eda524fa6adc3fb2e54513f80
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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