Cyclobutanol → HCID 58504641, compound

HRID 2367623Notes

Reaction equation

HRID 2367623 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.[NH2:27][C:28]1[N:33]=[C:32]([C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([F:42])[CH:35]=2)[CH:31]=[C:30]([N:43]2[CH2:48][CH2:47][CH2:46][C@@H:45]([NH2:49])[CH2:44]2)[N:29]=1>C(Cl)Cl>[CH:1]1([O:5][C:19](=[O:25])[NH:49][C@@H:45]2[CH2:46][CH2:47][CH2:48][N:43]([C:30]3[CH:31]=[C:32]([C:34]4[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([F:42])[CH:35]=4)[N:33]=[C:28]([NH2:27])[N:29]=3)[CH2:44]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 76218CyclobutanolHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 58504655HCID 58504655, compound

Product 1

HCID 58504641HCID 58504641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A premixed solution of cyclobutanol (30.5 μl, 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=411 [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-a6b2454a119345978b6b494d4e7a95ad
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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