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

HRID 1592632
Notes
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Reaction equation

HRID 1592632 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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)-N-(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-bff22d1b90564348912b1136f1db47a6
Source dataset
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07291631B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes