Bis(cyclohexylmethyl)amine → HCID 58379679, compound

HRID 1038990Notes

Reaction equation

HRID 1038990 reaction equation
[CH2:1]([N:4]([C@H:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)[C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][Cl:8])[CH:2]=[CH2:3].I[C:22]1[CH:23]=[C:24]2[CH2:39][C@@:29]3([C:37]4[C:32](=[N:33][CH:34]=[CH:35][CH:36]=4)[NH:31][C:30]3=[O:38])[CH2:28][C:25]2=[N:26][CH:27]=1.C1(CNCC2CCCCC2)CCCCC1>CN(C=O)C.[Pd].C(P(CCCC)CCCC)CCC.C(P(CCCC)CCCC)CCC>[Cl:8][CH2:7][C:6]([CH3:10])([CH3:9])[C:5]([N:4]([C@H:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)[CH2:1]/[CH:2]=[CH:3]/[C:22]1[CH:23]=[C:24]2[CH2:39][C@@:29]3([C:37]4[C:32](=[N:33][CH:34]=[CH:35][CH:36]=4)[NH:31][C:30]3=[O:38])[CH2:28][C:25]2=[N:26][CH:27]=1)=[O:11]

Participants

6

Reactant 3

HCID 4594378Bis(cyclohexylmethyl)amineHCID 58118681(6S)-3-Iodo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2' (1'H)-one2×HCID 58379695HCID 58379695, compound

Product 1

HCID 58379679HCID 58379679, compound

Reagents, catalysts & solvents 2

HCID 85567535HCID 85567535, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a degassed solution of N-allyl-3-chloro-N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2,2-dimethylpropanamide (110. mg, 0.377 mmol, prepared in Step B), (6S)-3-iodo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (137 mg, 0.377 mmol, Intermediate 7) and N,N-dicyclohexylmethylamine (81.0 mg, 0.415 mmol) in DMF (3.77 mL) was added bis-(tri-1-butylphosphine) palladium(0) (57.8 mg, 0.113 mmol). This solution was once again degassed, before being sealed and heated in a microwave at 120° C. for 20 minutes. The reaction mixture was then diluted with DCM and washed twice with half-saturated brine. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a residue. The residue was then applied to a silica gel column for purification, eluting with a gradient of 1-7% MeOH in DCM to provide the title compound. MS: m/z=527 (M+1).

Workup

  1. customThis solution was once again degassed
  2. custombefore being sealed
  3. additionThe reaction mixture was then diluted with DCM
  4. washwashed twice with half-saturated brine
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a residue
  9. customThe residue was then applied to a silica gel column for purification
  10. washeluting with a gradient of 1-7% MeOH in DCM

Sources & evidence

ORD record
ord-d601a1b2c4a242bc99d5b555d3a70ecb
Source dataset
uspto-grants-2013_10
Patent number
US08552023B2

Reaction notes

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