Cyclopropanecarbonyl chloride → HCID 57555298, compound

HRID 220993Notes

Reaction equation

HRID 220993 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([C:13](Cl)=[O:14])[CH2:12][CH2:11]1.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:35][CH2:34][C:33]3[S:32][C:31]([CH3:36])=[N:30][C:29]=3[C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]2=3)=[O:25])=[CH:20][C:19]=1[CH3:41]>ClCCl>[CH3:41][C:19]1[CH:20]=[C:21]([C:24]([N:26]2[CH2:35][CH2:34][C:33]3[S:32][C:31]([CH3:36])=[N:30][C:29]=3[C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]2=3)=[O:25])[CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][C:13]([CH:10]1[CH2:12][CH2:11]1)=[O:14]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 57555283HCID 57555283, compound

Product 1

HCID 57555298HCID 57555298, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIEA (0.02 ml, 0.115 mmol) and cyclopropanecarbonyl chloride (0.008 ml, 0.088 mmol) were added to a solution of (4-aminomethyl-3-methyl-phenyl)-(2-methyl-4,5-dihydro-3-thia-1,6-diaza-benzo[e]azulen-6-yl)-methanone from E124.2 (20 mg, 0.055 mmol) in dichloromethane (5 ml) at 0° C. The mixture was stirred for 20 h at room temperature then concentrated in vacuo and purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% di-chloromethane) to give a white powder identified as the title compound (11 mg, 46%).

Workup

  1. concentrationthen concentrated in vacuo
  2. custompurified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% di-chloromethane)
  3. customto give a white powder

Sources & evidence

ORD record
ord-4023ff122ecc4411a4d6e8a851b26cd9
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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