[(2R)-3-(2-{2-chloro-5-fluoro-6-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-4-pyrimidinyl}hydrazino)-2-(cyclopentyl methyl)-3-oxopropyl][(phenylmethyl)oxy]formamide → [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide

HRID 1366405Notes

Reaction equation

HRID 1366405 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:10](=[O:30])[C@H:11]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:12][N:13]([O:16]CC2C=CC=CC=2)[CH:14]=[O:15])[C:5]([F:31])=[C:4]([N:32]2[CH2:37][C@@H:36]3[CH2:38][C@H:33]2[CH2:34][N:35]3[CH3:39])[N:3]=1>CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:10](=[O:30])[C@H:11]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:12][N:13]([OH:16])[CH:14]=[O:15])[C:5]([F:31])=[C:4]([N:32]2[CH2:37][C@@H:36]3[CH2:38][C@H:33]2[CH2:34][N:35]3[CH3:39])[N:3]=1

Participants

3

Reactant 1

HCID 86636926[(2R)-3-(2-{2-chloro-5-fluoro-6-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-4-pyrimidinyl}hydrazino)-2-(cyclopentyl methyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

Product 1

HCID 58000777[(2R)-3-(2-{2-chloro-5-fluoro-6-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamideYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(2R)-3-(2-{2-chloro-5-fluoro-6-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (90 mg, 0.18 mmol) was dissolved in 3 mL of MeOH, degassed and placed under argon. 10% Pd/C (18 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for approximately 3 hrs. The contents were then degassed and filtered through Celite, and the Celite pad was washed with DCM and MeOH. The resulting filtrate was concentrated in vacuo to provide the pure [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (42 mg, 57%). LCMS: (M+H)+: 429.4.

Workup

  1. customdegassed
  2. addition10% Pd/C (18 mg) was added
  3. customthe contents were thoroughly degassed
  4. customfor approximately 3 hrs
  5. customThe contents were then degassed
  6. filtrationfiltered through Celite
  7. washthe Celite pad was washed with DCM and MeOH
  8. concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e7e189755bb44d70b55dba9f2fd0543b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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