N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → HCID 178426314, compound

HRID 251223Notes

Reaction equation

HRID 251223 reaction equation
[CH3:1][C:2]1[C:3]([N:8]([CH:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[CH2:9][CH2:10][CH2:11][NH2:12])=[N:4][CH:5]=[CH:6][CH:7]=1.C(OC(=O)[NH:29][C:30](=NC(OC(C)(C)C)=O)[N:31]1C=CC=N1)(C)(C)C.C(OC(=O)NC(CCCN(CC1C(C)=CC=CN=1)C1C2N=CC=CC=2CCC1)=NC(OC(C)(C)C)=O)(C)(C)C>C1COCC1>[CH3:1][C:2]1[C:3]([N:8]([CH:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[CH2:9][CH2:10][CH2:11][NH:12][C:30]([NH2:31])=[NH:29])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 67271945N1-(3-methyl-pyridin-2-yl)-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-propane-1,3-diamineHCID 86623813({3-[(3-Methyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-propyl}-tert-butoxycarbonylimino-methyl)-carbamic acid tert butyl ester

Product 1

HCID 178426314HCID 178426314, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N1-(3-methyl-pyridin-2-yl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-propane-1,3-diamine (63 mg, 0.20 mmol) and (tert-butoxycarbonylimino-pyrazol-1-yl-methyl)-carbamic acid tert-butyl ester (110 mg, 0.31 mmol) was stirred in THF (0.3 mL) for 16 hours. The solvent was removed under reduced pressure, CH2Cl2 (10 mL) was added and the organic phase washed with 15% aqueous NaOH solution (5×5 mL). The organic phase was then dried (Na2SO4) and concentrated under reduced pressure to afford, after column chromatography with silica gel (33:1:0.1 CH2Cl2/MeOH:NH4OH), ({3-[(3-methyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-propyl}-tert-butoxycarbonylimino-methyl)-carbamic acid tert butyl ester as a pale brown sticky solid (50 mg, 49%),

Workup

  1. customThe solvent was removed under reduced pressure, CH2Cl2 (10 mL)
  2. additionwas added
  3. washthe organic phase washed with 15% aqueous NaOH solution (5×5 mL)
  4. dry with materialThe organic phase was then dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford

Sources & evidence

ORD record
ord-6fc04c43209e4b12b8841c4a5fac2a48
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…