trans-2-Phenyl-1-cyclopropanecarbonyl chloride → HCID 67064043, compound

HRID 1409265Notes

Reaction equation

HRID 1409265 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH2:28])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1>N1C=CC=CC=1>[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH:28][C:10]([C@@H:8]3[CH2:9][C@H:7]3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:11])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1

Participants

4

Reactant 2

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chlorideHCID 58207181HCID 58207181, compound

Product 1

HCID 67064043HCID 67064043, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a round-bottomed flask was a mixture of (1R,2R)-2-phenylcyclopropanecarbonyl chloride and cis (+/+,−/−)-2-phenylcyclopropanecarbonyl chloride (200 mg, 1.1 mmol) added in Pyridine (5 mL) to give a yellow suspension. 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 124 mg, 0.554 mmol) was added portionwise at 0° C. The temperature was slowly raised to room temperature. The reaction was quenched with saturated sodium bicarbonate and partitioned between ethyl acetate and water. The separated organic layer was dried over Mg2SO4, filtered, and concentrated under reduced pressure (3×100 mL). The reaction mixture was filtered and purified by preparatory HPLC (70-80% MeCN/H2O gradient+0.01% TFA). Received 62 mg (30%) of yellow solid. Melting point (208.2-208.3° C.). 1H NMR (DMSO-d6) δ: 11.28 (s, 1H), 7.93-8.10 (m, 2H), 7.90 (s, 1H), 7.55-7.68 (m, 3H), 7.28-7.34 (m, 2H), 7.17-7.25 (m, 3H), 6.33 (s, 1H), 2.42-2.48 (m, 1H), 2.37 (s, 4H), 1.34-1.63 (m, 2H); [α]D20=−238° (c=1.058, MeOH). ESI-MS: m/z 369.0 (M+H)+.

Workup

  1. customIn a round-bottomed flask was
  2. customto give a yellow suspension
  3. customThe reaction was quenched with saturated sodium bicarbonate
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe separated organic layer was dried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (3×100 mL)
  8. filtrationThe reaction mixture was filtered
  9. custompurified by preparatory HPLC (70-80% MeCN/H2O gradient+0.01% TFA)
  10. customMelting point (208.2-208.3° C.)

Sources & evidence

ORD record
ord-6c2c2a6e6de147cba2e95a096eaddb29
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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