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 2068809Notes

Reaction equation

HRID 2068809 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
  2. dry with materialand brine, dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-dd8835e90a974b8b8caaa99415c56985
Source dataset
uspto-grants-2012_10
Patent number
US08299057B2

Reaction notes

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