Trifluoroacetic acid → tert-butyl 3-{[(4-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]phenyl)amino]methyl}azetidine-1-carboxylate

HRID 512979Notes

Reaction equation

HRID 512979 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:38]=[C:39]([F:41])[CH:40]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:37])[C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[N:24]([CH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[C:25](=[O:30])[C:26]([F:29])([F:28])[F:27].[CH:42]([CH:44]1[CH2:47][N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:45]1)=O.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>ClCCl>[F:41][C:39]1[CH:38]=[C:4]([CH:3]=[C:2]([F:1])[CH:40]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH2:42][CH:44]2[CH2:47][N:46]([C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49])[CH2:45]2)=[CH:19][C:18]=1[N:24]([CH:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1)[C:25](=[O:30])[C:26]([F:29])([F:27])[F:28])=[O:37]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10726182Tert-butyl 3-formylazetidine-1-carboxylateHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 86647628N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-amino-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide

Product 1

HCID 86647629tert-butyl 3-{[(4-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]phenyl)amino]methyl}azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-amino-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide (240 mg, 0.42 mmol) in dichloromethane (20 mL) were added tert-butyl 3-formylazetidine-1-carboxylate (116 mg, 0.63 mmol), trifluoroacetic acid (0.32 mL) and tetramethylammonium triacetoxyborohydride (165 mg g, 0.63 mmol). The mixture was stirred at room temperature overnight, then diluted with dichloromethane, washed with NaHCO3 sat. sol. and brine, dried over sodium sulfate and evaporated to dryness.

Workup

  1. washwashed with NaHCO3 sat. sol. and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f0ca37d135fd4d57a92e6fd8193e98a2
Source dataset
uspto-grants-2015_08
Patent number
US09102662B2

Reaction notes

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