1,1'-Carbonyldiimidazole → HCID 58386328, compound

HRID 64030Notes

Reaction equation

HRID 64030 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([NH2:22])=[C:15]3[N:14]=2)[CH:7]=1.CCN(C(C)C)C(C)C.C1N=CN([C:39]([N:41]2[CH:45]=N[CH:43]=[CH:42]2)=[O:40])C=1.N1CC[C@H:48]([OH:51])C1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([NH:22][C:39]([N:41]4[CH2:42][CH2:43][C@H:48]([OH:51])[CH2:45]4)=[O:40])=[C:15]3[N:14]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 67330818(R)-5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine

Product 1

HCID 58386328HCID 58386328, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM (5 mL) solution of (R)-5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (25 mg, 0.076 mmol) and DIEA (0.04 mL, 0.23 mmol) was added CDI (25 mg, 0.15 mmol) at ambient temperature in one portion. After stirring for one hour, (S)-pyrrolidin-3-ol (20 mg, 0.23 mmol) was added in one portion. The reaction was stirred overnight before it was concentrated and directly purified by reverse-phase column chromatography, eluting with 0 to 60% acetonitrile/water to yield the final product as a yellowish solid (28 mg, 83% yield). MS (apci) m/z=441.2 (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 60% acetonitrile/water

Sources & evidence

ORD record
ord-8362727315a74bd8a8f80f5d4b0a36c0
Source dataset
uspto-grants-2016_09
Patent number
US09447104B2

Reaction notes

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