HCID 58379677, compound → HCID 58379688, compound

HRID 1038987Notes

Reaction equation

HRID 1038987 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]#[C:17][C:18]1[CH:19]=[C:20]2[C:33](=[CH:34][CH:35]=1)[CH2:32][C:22]1([C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]1=[O:31])[CH2:21]2)[C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[CH2:1]([N:8]([CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[C:20]2[C:33](=[CH:34][CH:35]=1)[CH2:32][C:22]1([C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]1=[O:31])[CH2:21]2)[C:9](=[O:14])[C:10]([CH3:12])([CH3:13])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 58379677HCID 58379677, compoundHCID 178418361HCID 178418361, compound4×

Product 1

HCID 58379688HCID 58379688, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a nitrogen purged solution of N-Benzyl-2,2-dimethyl-N-[3-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-yl)prop-2-yn-1-yl]propanamide (42 mg, 0.91 mmol, Example 1) in MeOH (4 mL) was added 10% Pd/C (19 mg). The nitrogen atmosphere was exchanged for a hydrogen atmosphere using a hydrogen balloon, and then a fresh hydrogen balloon was attached. After 1 hour a mixture of alkene/alkane was observed. Allow reaction to stir for 20 hours under an atmosphere of hydrogen. The hydrogen atmosphere was then exchanged for a nitrogen atmosphere, and the mixture was filtered through celite, and washed with additional MeOH. The combined organics were concentrated in vacuo to yield 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 give the title compound. MS: m/z=468 (M+1). Human CGRP receptor binding Ki=45 nM. HRMS: m/z=468.2632; calculated m/z=468.2642 for C30H34N3O2.

Workup

  1. customAllow reaction
  2. filtrationthe mixture was filtered through celite
  3. washwashed with additional MeOH
  4. concentrationThe combined organics were concentrated in vacuo
  5. customto yield a residue
  6. customThe residue was then applied to a silica gel column for purification
  7. washeluting with a gradient of 1-7% MeOH in DCM

Sources & evidence

ORD record
ord-310e02f5ab014f659bc233068298152c
Source dataset
uspto-grants-2013_10
Patent number
US08552023B2

Reaction notes

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