Cyclopentanol → HCID 58504511, compound

HRID 2367622Notes

Reaction equation

HRID 2367622 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.ClC(Cl)(O[C:20](=[O:26])OC(Cl)(Cl)Cl)Cl.[NH2:28][C:29]1[N:34]=[C:33]([C:35]2[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[C:37]([F:43])[CH:36]=2)[CH:32]=[C:31]([N:44]2[CH2:49][CH2:48][CH2:47][C@@H:46]([NH2:50])[CH2:45]2)[N:30]=1>C(Cl)Cl>[CH:1]1([O:6][C:20](=[O:26])[NH:50][C@@H:46]2[CH2:47][CH2:48][CH2:49][N:44]([C:31]3[CH:32]=[C:33]([C:35]4[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[C:37]([F:43])[CH:36]=4)[N:34]=[C:29]([NH2:28])[N:30]=3)[CH2:45]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 58504655HCID 58504655, compound

Product 1

HCID 58504511HCID 58504511, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A premixed solution of cyclopentanol (33.5 mg, 0.389 mmol) and Hunig's base (57 uL) in CH2Cl2 (1 mL) was slowly added to a solution of triphosgene (38.5 mg, 0.130 mmol) in CH2Cl2 (1 mL), and the resulting solution was stirred for 1 hour. A premixed solution of 4-{2-amino-6-[(3R)-3-amino-1-piperidinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (125 mg, 0.324 mmol) and Hunig's base (226 uL) in CH2Cl2 (5 mL) was added, and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated, then loaded on a Biotage SNAP 10 g column and purified with a gradient of 0 to 55% EtOAc in Hexane over 25 min. LC-MS (ES) m/z=425 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. concentrationThe reaction was concentrated
  3. custompurified with a gradient of 0 to 55% EtOAc in Hexane over 25 min

Sources & evidence

ORD record
ord-e89d175dafcb4bbaa36e0f71a3d66f5e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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