HCID 86673834, compound → HCID 68283560, compound

HRID 1527383Notes

Reaction equation

HRID 1527383 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([F:10])[CH2:7][N:6]1[C:11]([NH:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([C:23]([NH2:25])=[O:24])[CH:15]=1)=[O:12])=[N+]=[N-]>C1COCC1>[NH2:1][CH2:4][C@@H:5]1[CH2:9][C@@H:8]([F:10])[CH2:7][N:6]1[C:11]([NH:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([C:23]([NH2:25])=[O:24])[CH:15]=1)=[O:12]

Participants

3

Reactant 1

HCID 86673834HCID 86673834, compound

Product 1

HCID 68283560HCID 68283560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[((2S,4R)-2-Azidomethyl-4-fluoro-pyrrolidine-1-carbonyl)-amino]-indole-1-carboxylic acid amide (500 mg, 2.84 mmol) was suspended in THF (5 mL). Air was removed from the flask and replaced with nitrogen three times. Pd/C 10% (100 mg) was added to the solution which was again degassed, placed under a hydrogen atmosphere, and stirred at RT for 1.5 h. The catalyst was removed through a pad of Celite and washed with THF and MeOH to give the desired material which was used in the next step without further purification. MS (LC-MS): 320.2 [M+H]+, 639.2 [2M+H]+, 661.3 [2M+Na]+, 318.1 [M−H]−; tR (HPLC conditions f): 0+1.02+1.61 min.

Workup

  1. customAir was removed from the flask
  2. additionPd/C 10% (100 mg) was added to the solution which
  3. customwas again degassed
  4. customThe catalyst was removed through a pad of Celite
  5. washwashed with THF and MeOH

Sources & evidence

ORD record
ord-f4567bd8c9824373b086451a434d594b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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