Toluene → HCID 178510929, compound

HRID 1012153Notes

Reaction equation

HRID 1012153 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[NH:16][C:15]([C:17]2[C:21]([NH:22][C:23](=[O:32])[C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])=[CH:20][N:19](C3CCCCO3)[N:18]=2)=[N:14][C:13]=1C(O)=O)=O)(C)(C)C.C1(OC)C=CC=CC=1.C1(C)C=CC=CC=1.[C:57]([OH:63])(C(F)(F)F)=[O:58]>>[NH2:8][CH2:9][CH2:10][CH2:11][C:12]1[NH:16][C:15]([C:17]2[C:21]([NH:22][C:23](=[O:32])[C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])=[CH:20][NH:19][N:18]=2)([C:57]([OH:63])=[O:58])[NH:14][CH:13]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 136395582HCID 136395582, compound

Product 1

HCID 178510929HCID 178510929, compoundYield 99%

Procedure

A solution of 5-(tert-butoxycarbonylamino-propyl)-2-[4-(2,6-difluoro benzoylamino)-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-3-yl]-1H-imidazole-4-carboxylic acid (300 mg, 0.52 mmoles) and anisole (114 μl, 1.04 mmoles) in TFA (3 ml) was heated at 100° C. (80 W) in a CEM discover microwave synthesizer for 10 minutes. Toluene (10 ml) was added and the solvent removed in vacuo to give 5-(3-amino-propyl)-2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-imidazole carboxylic acid as a yellow/brown solid (200 mg, 99%). (LC/MS: Rt 1.58, {M+H]+ 391.00).

Workup

  1. customfor 10 minutes
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7ea937b467f94aa2be61d68bf2ce50e1
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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