Dichloromethane → HCID 11950489, compound

HRID 507862Notes

Reaction equation

HRID 507862 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23](C)[N:22]=3)[CH2:16][CH2:15]1)[CH2:10]2)=[O:5])[CH3:2].[C:29](Cl)(=[O:31])[CH3:30].CCN(C(C)C)C(C)C.C(Cl)[Cl:43]>>[CH2:1]([O:3][C:4]([N:6]1[CH:7]2[CH2:13][CH2:12][CH:11]1[CH2:10][CH:9]([N:14]1[CH2:15][CH2:16][CH:17]([N:20]([C:29](=[O:31])[CH3:30])[C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([Cl:43])[N:22]=3)[CH2:18][CH2:19]1)[CH2:8]2)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68472675HCID 68472675, compound

Product 1

HCID 11950489HCID 11950489, compound

Conditions

Temperature
80 °C

Procedure

3-[4-(2,6-Dimethyl-pyrimidin-4-ylamino)piperidin-1-yl]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (20 mg; 0.05 mmol; 1 eq.) was dissolved in DCM (3 mL) and acetyl chloride (9.5 mg; 2.5 eq.) and DIEA (9.5 mg; 1.5 eq.) was added and the reaction was stirred overnight (approx. 14 hours) at 80° C. under N2. The solution was diluted with DCM (10 mL) and washed with saturated NaHCO3 (2×20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under high vacuum to provide the product as an oil (18 mg). The crude residue was purified by reversed-phase HPLC (2-99% CH3CN/water gradient with 0.05% TFA). M+1=450.2, Retention time=1.81 minutes; 10-99% CH3CN/H2O gradient with 0.05% TFA.

Workup

  1. washwashed with saturated NaHCO3 (2×20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-ca0c743274964dcbbbf194c31b2be669
Source dataset
uspto-grants-2010_08
Patent number
US07786308B2

Reaction notes

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