Water → HCID 49855401, compound

HRID 1260551Notes

Reaction equation

HRID 1260551 reaction equation
FC(F)(F)C(O)=O.[CH:8]([O:11][C:12]1[N:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]([NH2:29])[CH3:28])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)([CH3:10])[CH3:9].C(N(CC)CC)C.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1.O>ClCCl>[CH:8]([O:11][C:12]1[N:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH:27]([NH:29][C:40]([CH:37]3[CH2:39][CH2:38]3)=[O:41])[CH3:28])=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 67071742HCID 67071742, compound

Product 1

HCID 49855401HCID 49855401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[4-(6-Isopropoxypyridin-3-yloxy)phenyl]-1-methylpropylamine trifluoroacetate (115 mg, 0.28 mmol) and triethylamine (0.117 ml, 0.83 mmol) were dissolved in 5 ml of dichloromethane. Cyclopropanecarbonyl chloride (0.043 ml, 0.46 mmol) was added at 0° C. and the reaction mixture was stirred for 3 hours during which it warmed to room temperature. Following addition of water, the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 63 mg (62%), M+H+: 369.25.

Workup

  1. customthe organic phase was separated off
  2. concentrationconcentrated
  3. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-93149c464b8844a08e9646d4ce3d77d4
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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