1,1'-Carbonyldiimidazole → HCID 58386334, compound

HRID 63996Notes

Reaction equation

HRID 63996 reaction equation
[F:1][CH:2]([F:25])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[CH:20]=[CH:19][N:18]2[N:21]=[CH:22][C:23]([NH2:24])=[C:17]2[N:16]=1.C1N=CN([C:31]([N:33]2[CH:37]=N[CH:35]=[CH:34]2)=[O:32])C=1.Cl.N1CC([OH:43])C1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:25][CH:2]([F:1])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[CH:20]=[CH:19][N:18]2[N:21]=[CH:22][C:23]([NH:24][C:31]([N:33]3[CH2:34][CH:35]([OH:43])[CH2:37]3)=[O:32])=[C:17]2[N:16]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 67330428HCID 67330428, compound

Product 1

HCID 58386334HCID 58386334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM (0.6 mL) solution of (R)-5-(2-(2-(difluoromethyl)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (10 mg, 0.028 mmol, prepared as described in the following paragraph), was added CDI (9 mg, 0.056 mmol) at ambient temperature in one portion. After stirring two hours, azetidin-3-ol hydrochloride (6 mg, 0.056 mmol) was added in one portion, followed by addition of DIEA (0.015 mL, 0.084 mmol). The reaction was stirred overnight before it was concentrated and directly purified by reverse-phase column chromatography, eluting with 0 to 50% acetonitrile/water to yield the final product as a solid. MS (apci) m/z=447.2 (M+H).

Workup

  1. stirringThe reaction was stirred overnight before it
  2. concentrationwas concentrated
  3. customdirectly purified by reverse-phase column chromatography
  4. washeluting with 0 to 50% acetonitrile/water

Sources & evidence

ORD record
ord-9e00a2b645244944bdd4b9459bff9fb3
Source dataset
uspto-grants-2016_09
Patent number
US09447104B2

Reaction notes

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