1,1'-Carbonyldiimidazole → HCID 58386310, compound

HRID 2275363Notes

Reaction equation

HRID 2275363 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.N1CC[C@H:40]([OH:43])C1>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][CH2:35][C@@H:40]([OH:43])[CH2:37]3)=[O:32])=[C:17]2[N:16]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2733874(3S)-pyrrolidin-3-olHCID 67330428HCID 67330428, compound

Product 1

HCID 58386310HCID 58386310, compoundYield 69%

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, (S)-pyrrolidin-3-ol (8 mg, 0.084 mmol) was added in one portion. The reaction was stirred overnight, then concentrated and directly purified by reverse-phase column chromatography, eluting with 0 to 50% acetonitrile/water to yield the final product as a solid (9 mg, 69%). MS (apci) m/z=461.2 (M+H).

Workup

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

Sources & evidence

ORD record
ord-d9c54a4fb9174a959657cf9a5c135550
Source dataset
uspto-grants-2015_09
Patent number
US09127013B2

Reaction notes

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