Diisopropylethylamine → HCID 178522747, compound

HRID 2279644Notes

Reaction equation

HRID 2279644 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[N:2]1.CCN(C(C)C)C(C)C.Cl.[C:19]12([CH2:29][NH2:30])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(#N)C.CCOC(C)=O.O>[C:19]12([CH2:29][NH:30][C:6]([C:3]3[CH:4]=[CH:5][NH:1][N:2]=3)=[O:8])[CH2:26][CH:25]3[CH2:24][CH:23]([CH2:22][CH:21]([CH2:27]3)[CH2:20]1)[CH2:28]2

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 122929521-(Tricyclo[3.3.1.1~3,7~]decan-1-yl)methanamine--hydrogen chloride (1/1)HCID 178524567HCID 178524567, compound

Product 1

HCID 178522747HCID 178522747, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-pyrazole-3-carboxylic acid (594 mg, 5.3 mmol) in 20 mL ACN is added 2.3 mL of DIEA (13.25 mmol), followed by 1.28 g of adamantylmethylamine hydrochloride salt (6.36 mmol). The resulting mixture is stirred for 5 min at RT. 2.81 g of BOP (6.36 mmol) is added. The reaction mixture is stirred for 30 min at RT. The mixture is diluted with EtOAc and water. The organic layer is separated, and the aqueous layer is back extracted with EtOAc. The combined organic layers are washed with brine, dried over sodium sulfate and concentrated. The residue is triturated with DCM and air-dried to give the title compound.

Workup

  1. stirringThe reaction mixture is stirred for 30 min at RT
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is back extracted with EtOAc
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is triturated with DCM
  8. customair-dried

Sources & evidence

ORD record
ord-8dd1b89a77bd4a4183d95333255954d6
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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