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Diisopropylethylamine → HCID 25094826, compound

HRID 2039775
Notes
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Reaction equation

HRID 2039775 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:28][CH2:29][O:30][C:31]([C:33]1[CH:44]=[C:36]2[C:37]([C:41]([OH:43])=O)=[CH:38][CH:39]=[CH:40][N:35]2[N:34]=1)=[O:32].[C:45]12([CH2:55][NH2:56])[CH2:54][CH:49]3[CH2:50][CH:51]([CH2:53][CH:47]([CH2:48]3)[CH2:46]1)[CH2:52]2.CCN(C(C)C)C(C)C>CCOC(C)=O.CN(C=O)C>[CH2:29]([O:30][C:31]([C:33]1[CH:44]=[C:36]2[C:37]([C:41](=[O:43])[NH:56][CH2:55][C:45]34[CH2:54][CH:49]5[CH2:48][CH:47]([CH2:53][CH:51]([CH2:50]5)[CH2:52]3)[CH2:46]4)=[CH:38][CH:39]=[CH:40][N:35]2[N:34]=1)=[O:32])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59539022HCID 59539022, compound

Product 1

HCID 25094826HCID 25094826, compound

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

BOP (11 g, 24 mmol) is added to a slurry of pyrazolo[1,5-a]pyridine-2,4-dicarboxylic acid 2-ethyl ester (5.6 g, 24 mmol), adamantan-1-ylmethylamine (4.4 g, 27 mmol), iPr2NEt (21 mL, 120 mmol), and DMF (240 mL) under N2. The reaction vessel is sealed and the mixture is left to stir for 15 h. EtOAc (200 mL) is added. The solution is washed with 50% sat. aq. NH4Cl (2×500 mL). The aqueous phases are extracted with EtOAc (3×200 mL). The combined organics are dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography (2:1 hexanes:EtOAc to 1:1 hexanes:EtOAc) affords the title compound as a tan solid. 1H NMR (400 MHz, CDCl3) δ: 8.62 (d, 1H), 7.60 (d, 1H), 7.44 (s, 1H), 7.00 (t, 1H), 6.23 (bs, 1H), 4.48 (q, 2H), 3.23 (d, 2H), 1.98-2.07 (m, 3H), 1.57-1.78 (m, 12H), 1.45 (t, 3H). LC-MS m/z (M+H+): 382.2; RT=1.09 min.

Workup

  1. customThe reaction vessel is sealed
  2. waitthe mixture is left
  3. washThe solution is washed with 50% sat. aq. NH4Cl (2×500 mL)
  4. extractionThe aqueous phases are extracted with EtOAc (3×200 mL)
  5. dry with materialThe combined organics are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (2:1 hexanes:EtOAc to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-dbfc92be4c1a4389b0a9953b8d899807
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580812B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes