Isopropyl chloroformate → HCID 86629384, compound

HRID 1093298Notes

Reaction equation

HRID 1093298 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[N:9]=[CH:10][C:5]2=[C:4]([N:17]2[CH2:23][CH:22]3[O:24][CH:19]([CH2:20][CH2:21]3)[CH2:18]2)[N:3]=1.C(N(CC)CC)C.Cl[C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34]>ClCCl.C1(C)C=CC=CC=1>[CH:22]12[O:24][CH:19]([CH2:20][CH2:21]1)[CH2:18][N:17]([C:4]1[N:3]=[C:2]([Cl:1])[N:7]=[C:6]3[N:8]([CH:11]4[CH2:12][CH2:13][N:14]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:15][CH2:16]4)[N:9]=[CH:10][C:5]=13)[CH2:23]2

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 86629385HCID 86629385, compound

Product 1

HCID 86629384HCID 86629384, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

650 mg (1.7 mmol) of 3-(6-chloro-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane was suspended in 15 mL dichloromethane and triethylamine (0.5 mL) was added followed by addition of a 1N solution of isopropyl chloroformate in toluene. The mixture was stirred at room temperature overnight, diluted with dichloromethane and washed with sat. aqueous NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated to give 696 mg (1.6 mmol) of the title compound. MS: 435.3/437.3 [M+H].

Workup

  1. washwashed with sat. aqueous NaHCO3
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-281b82964f4844a6b2ebc2f3b2e08beb
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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