Acetic Acid → tert-butyl 2-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzylamino)-ethyl(methyl)carbamate

HRID 2196557Notes

Reaction equation

HRID 2196557 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH:14]=O)[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.[NH2:23][CH2:24][CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH2:14][NH:23][CH2:24][CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[N:9]=[C:8]([C:19]([F:22])([F:20])[F:21])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2756424N-Boc-N-methylethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 598432493-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzaldehyde

Product 1

HCID 59843190tert-butyl 2-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzylamino)-ethyl(methyl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of crude 122 (1.522 g, 4.97 mmol) in MeOH (20 mL) was added a solution of tert-butyl 2-aminoethyl(methyl)carbamate (1.732 g, 9.94 mmol, E. Atherton et al, J. Chem. Soc. C, 1971, 3393-3396) in MeOH (5 mL) followed by acetic acid (1.1 mL, 20 mmol). The reaction was stirred at room temperature for 1 hour then sodium cyanoborohydride (0.625 g, 9.94 mmol) was added and the resulting mixture was stirred for 16 hours. After the usual work-up crude 123 (2.30 g, 4.95 mmol, 100% yield) was obtained as yellow oil. LRMS(ESI): (calc.) 464.5 (found) 465.2 (MH)+, 487.2 (MNa)+.

Workup

  1. stirringthe resulting mixture was stirred for 16 hours

Sources & evidence

ORD record
ord-8611f6580c3a4fe0b28d241b3afba1fe
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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