Diisopropylethylamine → HCID 86694741, compound

HRID 475257Notes

Reaction equation

HRID 475257 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[N:23]1[C:31]2[C:26](=[C:27]([CH2:32][NH2:33])[CH:28]=[CH:29][CH:30]=2)[CH:25]=[N:24]1.CCN(C(C)C)C(C)C>CC(O)C>[CH:14]1([C:11]2[NH:12][N:13]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:33][CH2:32][C:27]4[CH:28]=[CH:29][CH:30]=[C:31]5[C:26]=4[CH:25]=[N:24][N:23]5[CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:17]4)[N:7]=3)[CH:10]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 226611964-aminomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleHCID 178478345HCID 178478345, compound

Product 1

HCID 86694741HCID 86694741, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A tube was charged with 53 (350 mg, 1.47 mmol), 199 (340 mg, 1.47 mmol), and DIPEA (5 mL) in IPA (10 mL), degassed, sealed and heated at 120° C. for 48 h. The solvent was evaporated in vacuo. The crude product was purified by SiO2 chromatography to afford 600 mg (94%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methyl)pyrimidine-2,4-diamine (200) as yellow solid: MS (ESI) m/z=431.2 [M+1]+.

Workup

  1. customdegassed
  2. customsealed
  3. customThe solvent was evaporated in vacuo
  4. customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-d37355f3d3d042c0bbd35cc86ed07593
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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